# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_huahl_0328_2
_database_code_depnum_ccdc_archive 'CCDC 1815728'
_audit_update_record             
;
2018-01-09 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2016-03-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        7-methyl-1-tosylindoline
_chemical_formula_moiety         'C16 H17 N O2 S'
_chemical_formula_sum            'C16 H17 N O2 S'
_chemical_formula_weight         287.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   15.2125(8)
_cell_length_b                   15.041(2)
_cell_length_c                   12.8713(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.483(5)
_cell_angle_gamma                90.00
_cell_volume                     2945.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1186
_cell_measurement_temperature    290.83(10)
_cell_measurement_theta_max      22.0770
_cell_measurement_theta_min      3.6990
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.1338
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11725
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.38
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.83(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -38.00   71.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega    0.00   58.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
  4 omega  -57.00  -26.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  120.0000  141.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0079283000
_diffrn_orient_matrix_UB_12      -0.0464357000
_diffrn_orient_matrix_UB_13      -0.0029952000
_diffrn_orient_matrix_UB_21      0.0455835000
_diffrn_orient_matrix_UB_22      -0.0083108000
_diffrn_orient_matrix_UB_23      0.0066468000
_diffrn_orient_matrix_UB_31      -0.0055788000
_diffrn_orient_matrix_UB_32      -0.0015395000
_diffrn_orient_matrix_UB_33      0.0546046000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2267
_reflns_number_total             5798
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1895
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0373P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1784
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15), C19(H19),
 C20(H20), C21(H21), C27(H27), C28(H28), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.20762(7) 0.21802(11) 0.28509(9) 0.0690(5) Uani 1 d . . .
O1 O 0.26223(17) 0.2798(3) 0.2302(2) 0.0821(12) Uani 1 d . . .
O2 O 0.23890(19) 0.1786(3) 0.3796(2) 0.0922(13) Uani 1 d . . .
N1 N 0.1168(2) 0.2724(3) 0.3167(2) 0.0562(11) Uani 1 d . . .
C1 C 0.0660(3) 0.3146(4) 0.2348(3) 0.0527(13) Uani 1 d . . .
C2 C 0.0875(3) 0.3927(4) 0.1832(3) 0.0581(14) Uani 1 d . . .
C3 C 0.0248(3) 0.4223(4) 0.1104(3) 0.0712(16) Uani 1 d . . .
H3 H 0.0356 0.4744 0.0736 0.085 Uiso 1 calc . . R
C4 C -0.0519(3) 0.3770(5) 0.0916(3) 0.0751(18) Uani 1 d . . .
H4 H -0.0901 0.3971 0.0398 0.090 Uiso 1 calc . . R
C5 C -0.0736(3) 0.3026(4) 0.1478(3) 0.0668(16) Uani 1 d . . .
H5 H -0.1269 0.2738 0.1368 0.080 Uiso 1 calc . . R
C6 C -0.0143(3) 0.2719(4) 0.2206(3) 0.0594(14) Uani 1 d . . .
C7 C -0.0218(3) 0.1969(4) 0.2963(3) 0.0719(16) Uani 1 d . . .
H7A H -0.0121 0.1400 0.2627 0.086 Uiso 1 calc . . R
H7B H -0.0790 0.1964 0.3290 0.086 Uiso 1 calc . . R
C8 C 0.0513(3) 0.2173(4) 0.3754(3) 0.0690(16) Uani 1 d . . .
H8A H 0.0282 0.2502 0.4340 0.083 Uiso 1 calc . . R
H8B H 0.0781 0.1629 0.4007 0.083 Uiso 1 calc . . R
C9 C 0.1690(3) 0.4469(4) 0.2028(3) 0.0866(18) Uani 1 d . . .
H9A H 0.1885 0.4383 0.2732 0.130 Uiso 1 calc . . GR
H9B H 0.1563 0.5086 0.1915 0.130 Uiso 1 calc . . GR
H9C H 0.2144 0.4282 0.1562 0.130 Uiso 1 calc . . GR
C10 C 0.1781(2) 0.1325(4) 0.1998(3) 0.0586(15) Uani 1 d . . .
C11 C 0.1725(3) 0.1501(4) 0.0941(4) 0.0674(15) Uani 1 d . . .
H11 H 0.1853 0.2066 0.0691 0.081 Uiso 1 calc . . R
C12 C 0.1477(3) 0.0833(5) 0.0259(4) 0.0726(17) Uani 1 d . . .
H12 H 0.1449 0.0949 -0.0450 0.087 Uiso 1 calc . . R
C13 C 0.1268(3) -0.0010(5) 0.0625(5) 0.0718(17) Uani 1 d . . .
C14 C 0.1312(3) -0.0172(4) 0.1669(5) 0.0792(17) Uani 1 d . . .
H14 H 0.1171 -0.0733 0.1920 0.095 Uiso 1 calc . . R
C15 C 0.1561(3) 0.0483(5) 0.2347(4) 0.0722(17) Uani 1 d . . .
H15 H 0.1582 0.0362 0.3056 0.087 Uiso 1 calc . . R
C16 C 0.1017(3) -0.0751(5) -0.0130(4) 0.099(2) Uani 1 d . . .
H16A H 0.0516 -0.0570 -0.0537 0.148 Uiso 1 calc . . GR
H16B H 0.0875 -0.1279 0.0253 0.148 Uiso 1 calc . . GR
H16C H 0.1502 -0.0871 -0.0582 0.148 Uiso 1 calc . . GR
S2 S 0.70704(7) 0.20950(11) 0.37396(8) 0.0652(5) Uani 1 d . . .
O3 O 0.73498(17) 0.2185(3) 0.26861(19) 0.0852(13) Uani 1 d . . .
O4 O 0.76402(17) 0.1684(3) 0.4487(2) 0.0800(12) Uani 1 d . . .
N2 N 0.61540(19) 0.1490(3) 0.3696(2) 0.0564(12) Uani 1 d . . .
C17 C 0.5660(2) 0.1388(4) 0.4654(3) 0.0528(13) Uani 1 d . . .
C18 C 0.5887(3) 0.0827(4) 0.5482(3) 0.0603(14) Uani 1 d . . .
C19 C 0.5264(3) 0.0808(4) 0.6281(3) 0.0735(17) Uani 1 d . . .
H19 H 0.5382 0.0466 0.6868 0.088 Uiso 1 calc . . R
C20 C 0.4491(3) 0.1273(5) 0.6231(4) 0.0792(19) Uani 1 d . . .
H20 H 0.4103 0.1240 0.6784 0.095 Uiso 1 calc . . R
C21 C 0.4276(3) 0.1788(4) 0.5385(3) 0.0698(16) Uani 1 d . . .
H21 H 0.3749 0.2101 0.5354 0.084 Uiso 1 calc . . R
C22 C 0.4872(3) 0.1823(4) 0.4582(3) 0.0575(14) Uani 1 d . . .
C23 C 0.4775(2) 0.2268(4) 0.3543(3) 0.0707(17) Uani 1 d . . .
H23A H 0.4879 0.2903 0.3594 0.085 Uiso 1 calc . . R
H23B H 0.4197 0.2166 0.3244 0.085 Uiso 1 calc . . R
C24 C 0.5484(2) 0.1814(4) 0.2919(3) 0.0680(17) Uani 1 d . . .
H24A H 0.5240 0.1320 0.2527 0.082 Uiso 1 calc . . R
H24B H 0.5749 0.2229 0.2437 0.082 Uiso 1 calc . . R
C25 C 0.6689(3) 0.0265(4) 0.5547(3) 0.0883(18) Uani 1 d . . .
H25A H 0.6849 0.0073 0.4863 0.132 Uiso 1 calc . . GR
H25B H 0.6574 -0.0245 0.5973 0.132 Uiso 1 calc . . GR
H25C H 0.7162 0.0603 0.5847 0.132 Uiso 1 calc . . GR
C26 C 0.6804(2) 0.3151(4) 0.4211(3) 0.0591(15) Uani 1 d . . .
C27 C 0.6638(3) 0.3848(5) 0.3526(4) 0.0720(16) Uani 1 d . . .
H27 H 0.6675 0.3761 0.2812 0.086 Uiso 1 calc . . R
C28 C 0.6416(3) 0.4672(5) 0.3926(5) 0.0802(18) Uani 1 d . . .
H28 H 0.6299 0.5137 0.3468 0.096 Uiso 1 calc . . R
C29 C 0.6365(3) 0.4825(5) 0.4970(5) 0.0779(17) Uani 1 d . . .
C30 C 0.6550(3) 0.4133(5) 0.5632(4) 0.0809(19) Uani 1 d . . .
H30 H 0.6528 0.4229 0.6345 0.097 Uiso 1 calc . . R
C31 C 0.6770(3) 0.3301(4) 0.5268(3) 0.0669(15) Uani 1 d . . .
H31 H 0.6894 0.2843 0.5732 0.080 Uiso 1 calc . . R
C32 C 0.6136(4) 0.5744(5) 0.5374(5) 0.118(2) Uani 1 d . . .
H32A H 0.5699 0.5693 0.5904 0.177 Uiso 1 calc . . GR
H32B H 0.5911 0.6101 0.4813 0.177 Uiso 1 calc . . GR
H32C H 0.6654 0.6019 0.5659 0.177 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.437(3) . ?
S1 O2 1.431(3) . ?
S1 N1 1.658(3) . ?
S1 C10 1.747(6) . ?
N1 C1 1.448(5) . ?
N1 C8 1.505(5) . ?
C1 C2 1.391(7) . ?
C1 C6 1.391(6) . ?
C2 C3 1.404(5) . ?
C2 C9 1.503(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(6) . ?
C6 C7 1.496(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.532(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.388(5) . ?
C10 C15 1.385(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(8) . ?
C13 C14 1.367(6) . ?
C13 C16 1.525(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(7) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
S2 O3 1.431(3) . ?
S2 O4 1.430(3) . ?
S2 N2 1.666(4) . ?
S2 C26 1.750(6) . ?
N2 C17 1.457(4) . ?
N2 C24 1.503(4) . ?
C17 C18 1.400(6) . ?
C17 C22 1.369(5) . ?
C18 C19 1.404(5) . ?
C18 C25 1.487(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(5) . ?
C22 C23 1.501(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.514(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.391(7) . ?
C26 C31 1.379(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.385(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.366(6) . ?
C29 C30 1.372(8) . ?
C29 C32 1.518(8) . ?
C30 H30 0.9300 . ?
C30 C31 1.379(8) . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 106.7(2) . . ?
O1 S1 C10 108.3(2) . . ?
O2 S1 O1 119.8(2) . . ?
O2 S1 N1 105.53(18) . . ?
O2 S1 C10 108.1(3) . . ?
N1 S1 C10 107.86(19) . . ?
C1 N1 S1 118.6(2) . . ?
C1 N1 C8 104.8(3) . . ?
C8 N1 S1 114.1(3) . . ?
C2 C1 N1 126.3(4) . . ?
C2 C1 C6 122.5(4) . . ?
C6 C1 N1 110.9(4) . . ?
C1 C2 C3 115.2(5) . . ?
C1 C2 C9 125.0(4) . . ?
C3 C2 C9 119.7(5) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.2(5) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(5) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.3(5) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C7 109.5(4) . . ?
C5 C6 C1 120.3(5) . . ?
C5 C6 C7 130.1(5) . . ?
C6 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C6 C7 C8 102.9(4) . . ?
H7A C7 H7B 109.1 . . ?
C8 C7 H7A 111.2 . . ?
C8 C7 H7B 111.2 . . ?
N1 C8 C7 104.9(3) . . ?
N1 C8 H8A 110.8 . . ?
N1 C8 H8B 110.8 . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.8 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 S1 119.3(5) . . ?
C15 C10 S1 122.0(4) . . ?
C15 C10 C11 118.6(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(5) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(5) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C16 120.5(5) . . ?
C14 C13 C12 119.0(6) . . ?
C14 C13 C16 120.4(6) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.7(6) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.1(5) . . ?
C14 C15 H15 119.4 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 S2 N2 105.96(17) . . ?
O3 S2 C26 108.3(3) . . ?
O4 S2 O3 119.71(19) . . ?
O4 S2 N2 106.8(2) . . ?
O4 S2 C26 107.4(2) . . ?
N2 S2 C26 108.18(19) . . ?
C17 N2 S2 117.8(2) . . ?
C17 N2 C24 104.2(3) . . ?
C24 N2 S2 114.1(3) . . ?
C18 C17 N2 125.6(4) . . ?
C22 C17 N2 110.5(4) . . ?
C22 C17 C18 123.3(4) . . ?
C17 C18 C19 114.0(4) . . ?
C17 C18 C25 125.6(4) . . ?
C19 C18 C25 120.4(5) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 C18 122.6(5) . . ?
C20 C19 H19 118.7 . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.6(5) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 121.3 . . ?
C20 C21 C22 117.5(5) . . ?
C22 C21 H21 121.3 . . ?
C17 C22 C21 120.8(4) . . ?
C17 C22 C23 110.6(3) . . ?
C21 C22 C23 128.6(4) . . ?
C22 C23 H23A 111.4 . . ?
C22 C23 H23B 111.4 . . ?
C22 C23 C24 101.9(4) . . ?
H23A C23 H23B 109.2 . . ?
C24 C23 H23A 111.4 . . ?
C24 C23 H23B 111.4 . . ?
N2 C24 C23 106.0(3) . . ?
N2 C24 H24A 110.5 . . ?
N2 C24 H24B 110.5 . . ?
C23 C24 H24A 110.5 . . ?
C23 C24 H24B 110.5 . . ?
H24A C24 H24B 108.7 . . ?
C18 C25 H25A 109.5 . . ?
C18 C25 H25B 109.5 . . ?
C18 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 S2 120.3(4) . . ?
C31 C26 S2 120.0(5) . . ?
C31 C26 C27 119.6(5) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 C26 118.8(5) . . ?
C28 C27 H27 120.6 . . ?
C27 C28 H28 118.9 . . ?
C29 C28 C27 122.1(6) . . ?
C29 C28 H28 118.9 . . ?
C28 C29 C30 118.1(6) . . ?
C28 C29 C32 120.3(7) . . ?
C30 C29 C32 121.6(6) . . ?
C29 C30 H30 119.1 . . ?
C29 C30 C31 121.8(5) . . ?
C31 C30 H30 119.1 . . ?
C26 C31 H31 120.2 . . ?
C30 C31 C26 119.6(6) . . ?
C30 C31 H31 120.2 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 -74.9(6) . . . . ?
S1 N1 C1 C6 111.6(4) . . . . ?
S1 N1 C8 C7 -105.4(4) . . . . ?
S1 C10 C11 C12 -178.9(3) . . . . ?
S1 C10 C15 C14 178.5(3) . . . . ?
O1 S1 N1 C1 55.8(4) . . . . ?
O1 S1 N1 C8 -180.0(3) . . . . ?
O1 S1 C10 C11 -28.5(4) . . . . ?
O1 S1 C10 C15 154.6(4) . . . . ?
O2 S1 N1 C1 -175.7(4) . . . . ?
O2 S1 N1 C8 -51.5(3) . . . . ?
O2 S1 C10 C11 -159.7(3) . . . . ?
O2 S1 C10 C15 23.4(4) . . . . ?
N1 S1 C10 C11 86.7(4) . . . . ?
N1 S1 C10 C15 -90.3(4) . . . . ?
N1 C1 C2 C3 -176.9(4) . . . . ?
N1 C1 C2 C9 0.9(8) . . . . ?
N1 C1 C6 C5 178.7(4) . . . . ?
N1 C1 C6 C7 0.9(5) . . . . ?
C1 N1 C8 C7 25.9(5) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C1 C6 C7 C8 15.3(5) . . . . ?
C2 C1 C6 C5 4.9(7) . . . . ?
C2 C1 C6 C7 -172.9(4) . . . . ?
C2 C3 C4 C5 3.7(8) . . . . ?
C3 C4 C5 C6 -3.0(8) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
C4 C5 C6 C7 176.1(5) . . . . ?
C5 C6 C7 C8 -162.2(5) . . . . ?
C6 C1 C2 C3 -4.0(7) . . . . ?
C6 C1 C2 C9 173.7(4) . . . . ?
C6 C7 C8 N1 -25.0(5) . . . . ?
C8 N1 C1 C2 156.4(5) . . . . ?
C8 N1 C1 C6 -17.1(5) . . . . ?
C9 C2 C3 C4 -178.0(4) . . . . ?
C10 S1 N1 C1 -60.4(4) . . . . ?
C10 S1 N1 C8 63.8(3) . . . . ?
C10 C11 C12 C13 1.1(7) . . . . ?
C11 C10 C15 C14 1.6(7) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C11 C12 C13 C16 -178.5(4) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C13 C14 C15 C10 -0.5(8) . . . . ?
C15 C10 C11 C12 -1.8(6) . . . . ?
C16 C13 C14 C15 178.2(4) . . . . ?
S2 N2 C17 C18 -76.5(5) . . . . ?
S2 N2 C17 C22 112.0(4) . . . . ?
S2 N2 C24 C23 -104.7(4) . . . . ?
S2 C26 C27 C28 179.1(4) . . . . ?
S2 C26 C31 C30 -179.3(4) . . . . ?
O3 S2 N2 C17 -172.3(3) . . . . ?
O3 S2 N2 C24 -49.7(4) . . . . ?
O3 S2 C26 C27 18.5(4) . . . . ?
O3 S2 C26 C31 -160.6(3) . . . . ?
O4 S2 N2 C17 59.1(4) . . . . ?
O4 S2 N2 C24 -178.3(3) . . . . ?
O4 S2 C26 C27 149.1(4) . . . . ?
O4 S2 C26 C31 -30.0(4) . . . . ?
N2 S2 C26 C27 -96.0(4) . . . . ?
N2 S2 C26 C31 85.0(4) . . . . ?
N2 C17 C18 C19 -175.7(4) . . . . ?
N2 C17 C18 C25 2.6(7) . . . . ?
N2 C17 C22 C21 177.4(4) . . . . ?
N2 C17 C22 C23 -0.4(5) . . . . ?
C17 N2 C24 C23 25.1(5) . . . . ?
C17 C18 C19 C20 2.3(7) . . . . ?
C17 C22 C23 C24 15.9(5) . . . . ?
C18 C17 C22 C21 5.6(7) . . . . ?
C18 C17 C22 C23 -172.2(4) . . . . ?
C18 C19 C20 C21 0.3(8) . . . . ?
C19 C20 C21 C22 -0.2(8) . . . . ?
C20 C21 C22 C17 -2.6(7) . . . . ?
C20 C21 C22 C23 174.7(5) . . . . ?
C21 C22 C23 C24 -161.7(5) . . . . ?
C22 C17 C18 C19 -5.2(7) . . . . ?
C22 C17 C18 C25 173.1(5) . . . . ?
C22 C23 C24 N2 -24.7(5) . . . . ?
C24 N2 C17 C18 156.1(5) . . . . ?
C24 N2 C17 C22 -15.5(5) . . . . ?
C25 C18 C19 C20 -176.1(5) . . . . ?
C26 S2 N2 C17 -56.3(4) . . . . ?
C26 S2 N2 C24 66.3(3) . . . . ?
C26 C27 C28 C29 0.7(8) . . . . ?
C27 C26 C31 C30 1.6(7) . . . . ?
C27 C28 C29 C30 0.7(8) . . . . ?
C27 C28 C29 C32 178.9(5) . . . . ?
C28 C29 C30 C31 -1.0(8) . . . . ?
C29 C30 C31 C26 -0.1(8) . . . . ?
C31 C26 C27 C28 -1.9(7) . . . . ?
C32 C29 C30 C31 -179.1(5) . . . . ?

_olex2_date_sample_data_collection 2016-03-28
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_liuc_547_2
_database_code_depnum_ccdc_archive 'CCDC 1815739'
_audit_update_record             
;
2018-01-09 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2017-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_name_common            ?
_chemical_name_systematic        
(R)-1-((4-bromophenyl)sulfonyl)-2-phenyl-2,3-dihydro-1H-benzo[g]indole
_chemical_formula_moiety         'C24 H18 Br N O2 S'
_chemical_formula_sum            'C24 H18 Br N O2 S'
_chemical_formula_weight         464.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   11.2737(10)
_cell_length_b                   8.0033(8)
_cell_length_c                   11.9357(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.605(9)
_cell_angle_gamma                90.00
_cell_volume                     1020.64(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    807
_cell_measurement_temperature    289.50(10)
_cell_measurement_theta_max      24.9940
_cell_measurement_theta_min      3.8060
_exptl_absorpt_coefficient_mu    2.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3728
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      289.50(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -97.00  -58.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega    8.00   66.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00   86.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000   90.0000 80
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0535642000
_diffrn_orient_matrix_UB_12      -0.0521785000
_diffrn_orient_matrix_UB_13      0.0139267000
_diffrn_orient_matrix_UB_21      -0.0387964000
_diffrn_orient_matrix_UB_22      -0.0716321000
_diffrn_orient_matrix_UB_23      -0.0069876000
_diffrn_orient_matrix_UB_31      -0.0052445000
_diffrn_orient_matrix_UB_32      -0.0038427000
_diffrn_orient_matrix_UB_33      -0.0607621000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1913
_reflns_number_total             2564
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(13)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0305P)²+0.0412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br -0.49918(6) -0.06759(13) -0.15593(6) 0.0735(3) Uani 1 d . . .
S1 S -0.86848(14) -0.6671(2) -0.39326(11) 0.0380(4) Uani 1 d . . .
O1 O -0.7998(4) -0.8201(6) -0.3666(3) 0.0487(13) Uani 1 d . . .
O2 O -0.9358(4) -0.6272(6) -0.5137(3) 0.0507(14) Uani 1 d . . .
N1 N -0.9743(4) -0.6699(7) -0.3230(3) 0.0340(11) Uani 1 d . . .
C1 C -0.9251(5) -0.6687(9) -0.1945(4) 0.0315(13) Uani 1 d . . .
C2 C -0.8687(5) -0.8019(8) -0.1214(4) 0.0345(15) Uani 1 d . . .
C3 C -0.8556(5) -0.9661(9) -0.1596(5) 0.0406(16) Uani 1 d . . .
H3 H -0.8862 -0.9914 -0.2397 0.049 Uiso 1 calc . . R
C4 C -0.7991(5) -1.0872(11) -0.0812(5) 0.0504(18) Uani 1 d . . .
H4 H -0.7946 -1.1950 -0.1086 0.061 Uiso 1 calc . . R
C5 C -0.7478(6) -1.0544(13) 0.0393(5) 0.0602(19) Uani 1 d . . .
H5 H -0.7062 -1.1379 0.0913 0.072 Uiso 1 calc . . R
C6 C -0.7594(6) -0.8986(11) 0.0797(5) 0.054(2) Uani 1 d . . .
H6 H -0.7253 -0.8769 0.1602 0.065 Uiso 1 calc . . R
C7 C -0.8219(5) -0.7675(10) 0.0032(5) 0.0416(16) Uani 1 d . . .
C8 C -0.8425(5) -0.6110(10) 0.0457(5) 0.047(2) Uani 1 d . . .
H8 H -0.8112 -0.5899 0.1265 0.057 Uiso 1 calc . . R
C9 C -0.9077(5) -0.4872(9) -0.0288(5) 0.0451(17) Uani 1 d . . .
H9 H -0.9244 -0.3858 0.0012 0.054 Uiso 1 calc . . R
C10 C -0.9490(5) -0.5180(8) -0.1525(4) 0.0350(16) Uani 1 d . . .
C11 C -1.0221(5) -0.4045(8) -0.2510(4) 0.0419(16) Uani 1 d . . .
H11A H -0.9691 -0.3201 -0.2690 0.050 Uiso 1 calc . . R
H11B H -1.0909 -0.3507 -0.2329 0.050 Uiso 1 calc . . R
C12 C -1.0694(5) -0.5335(9) -0.3530(4) 0.0395(16) Uani 1 d . . .
H12 H -1.0720 -0.4817 -0.4282 0.047 Uiso 1 calc . . R
C13 C -1.1981(5) -0.6002(9) -0.3614(4) 0.0374(17) Uani 1 d . . .
C14 C -1.2183(6) -0.7631(11) -0.3329(5) 0.0506(19) Uani 1 d . . .
H14 H -1.1523 -0.8386 -0.3100 0.061 Uiso 1 calc . . R
C15 C -1.3372(7) -0.8122(11) -0.3387(5) 0.065(2) Uani 1 d . . .
H15 H -1.3497 -0.9214 -0.3182 0.077 Uiso 1 calc . . R
C16 C -1.4369(6) -0.7074(13) -0.3732(6) 0.067(3) Uani 1 d . . .
H16 H -1.5163 -0.7438 -0.3769 0.081 Uiso 1 calc . . R
C17 C -1.4172(6) -0.5447(14) -0.4030(5) 0.061(2) Uani 1 d . . .
H17 H -1.4841 -0.4705 -0.4270 0.073 Uiso 1 calc . . R
C18 C -1.2997(5) -0.4926(10) -0.3971(4) 0.054(2) Uani 1 d . . .
H18 H -1.2877 -0.3832 -0.4173 0.065 Uiso 1 calc . . R
C19 C -0.7644(5) -0.5025(8) -0.3317(4) 0.0332(16) Uani 1 d . . .
C20 C -0.6646(5) -0.5320(10) -0.2274(4) 0.0455(18) Uani 1 d . . .
H20 H -0.6516 -0.6377 -0.1934 0.055 Uiso 1 calc . . R
C21 C -0.5862(6) -0.4014(10) -0.1765(5) 0.0501(19) Uani 1 d . . .
H21 H -0.5203 -0.4172 -0.1068 0.060 Uiso 1 calc . . R
C22 C -0.6068(5) -0.2488(10) -0.2297(5) 0.0440(17) Uani 1 d . . .
C23 C -0.7020(5) -0.2163(9) -0.3322(5) 0.0425(17) Uani 1 d . . .
H23 H -0.7136 -0.1105 -0.3662 0.051 Uiso 1 calc . . R
C24 C -0.7801(6) -0.3482(9) -0.3825(5) 0.0386(16) Uani 1 d . . .
H24 H -0.8449 -0.3311 -0.4528 0.046 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C22 1.916(7) . ?
S1 O1 1.430(5) . ?
S1 O2 1.431(3) . ?
S1 N1 1.663(4) . ?
S1 C19 1.762(6) . ?
N1 C1 1.455(6) . ?
N1 C12 1.491(8) . ?
C1 C2 1.396(8) . ?
C1 C10 1.365(8) . ?
C2 C3 1.414(9) . ?
C2 C7 1.438(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.359(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.421(10) . ?
C7 C8 1.398(10) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.422(7) . ?
C10 C11 1.507(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.555(8) . ?
C12 H12 0.9800 . ?
C12 C13 1.519(8) . ?
C13 C14 1.384(10) . ?
C13 C18 1.387(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.356(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(12) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.406(7) . ?
C19 C24 1.362(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(10) . ?
C21 H21 0.9300 . ?
C21 C22 1.362(10) . ?
C22 C23 1.370(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(9) . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.4(3) . . ?
O1 S1 N1 107.5(3) . . ?
O1 S1 C19 107.8(3) . . ?
O2 S1 N1 105.9(2) . . ?
O2 S1 C19 108.7(3) . . ?
N1 S1 C19 106.9(2) . . ?
C1 N1 S1 116.0(3) . . ?
C1 N1 C12 104.5(4) . . ?
C12 N1 S1 116.4(4) . . ?
C2 C1 N1 126.7(6) . . ?
C10 C1 N1 109.8(5) . . ?
C10 C1 C2 123.3(4) . . ?
C1 C2 C3 125.6(5) . . ?
C1 C2 C7 116.4(6) . . ?
C3 C2 C7 118.0(6) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.7(8) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.9(8) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.3(6) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 117.8(7) . . ?
C8 C7 C2 119.9(6) . . ?
C8 C7 C6 122.3(6) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.8(5) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.5(6) . . ?
C10 C9 H9 120.8 . . ?
C1 C10 C9 119.8(6) . . ?
C1 C10 C11 111.7(5) . . ?
C9 C10 C11 128.5(6) . . ?
C10 C11 H11A 111.7 . . ?
C10 C11 H11B 111.7 . . ?
C10 C11 C12 100.1(5) . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11A 111.7 . . ?
C12 C11 H11B 111.7 . . ?
N1 C12 C11 105.0(4) . . ?
N1 C12 H12 109.8 . . ?
N1 C12 C13 110.9(5) . . ?
C11 C12 H12 109.8 . . ?
C13 C12 C11 111.5(4) . . ?
C13 C12 H12 109.8 . . ?
C14 C13 C12 122.9(6) . . ?
C14 C13 C18 118.4(6) . . ?
C18 C13 C12 118.7(6) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(7) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.5(8) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.3(7) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(8) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.2(8) . . ?
C17 C18 H18 119.4 . . ?
C20 C19 S1 118.8(5) . . ?
C24 C19 S1 121.2(4) . . ?
C24 C19 C20 120.0(6) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.8(7) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.0(6) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 Br1 118.4(5) . . ?
C21 C22 C23 123.7(7) . . ?
C23 C22 Br1 117.9(6) . . ?
C22 C23 H23 121.6 . . ?
C22 C23 C24 116.8(6) . . ?
C24 C23 H23 121.6 . . ?
C19 C24 C23 121.6(5) . . ?
C19 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C22 C23 C24 -178.7(4) . . . . ?
S1 N1 C1 C2 -74.4(7) . . . . ?
S1 N1 C1 C10 109.4(5) . . . . ?
S1 N1 C12 C11 -99.9(4) . . . . ?
S1 N1 C12 C13 139.6(4) . . . . ?
S1 C19 C20 C21 -177.3(4) . . . . ?
S1 C19 C24 C23 177.2(4) . . . . ?
O1 S1 N1 C1 65.3(5) . . . . ?
O1 S1 N1 C12 -171.1(4) . . . . ?
O1 S1 C19 C20 -31.4(5) . . . . ?
O1 S1 C19 C24 149.5(5) . . . . ?
O2 S1 N1 C1 -166.0(5) . . . . ?
O2 S1 N1 C12 -42.4(4) . . . . ?
O2 S1 C19 C20 -162.2(4) . . . . ?
O2 S1 C19 C24 18.6(6) . . . . ?
N1 S1 C19 C20 84.0(5) . . . . ?
N1 S1 C19 C24 -95.2(5) . . . . ?
N1 C1 C2 C3 -3.8(9) . . . . ?
N1 C1 C2 C7 177.1(5) . . . . ?
N1 C1 C10 C9 -179.1(4) . . . . ?
N1 C1 C10 C11 2.2(6) . . . . ?
N1 C12 C13 C14 5.9(7) . . . . ?
N1 C12 C13 C18 -175.4(4) . . . . ?
C1 N1 C12 C11 29.5(6) . . . . ?
C1 N1 C12 C13 -91.1(5) . . . . ?
C1 C2 C3 C4 -179.9(5) . . . . ?
C1 C2 C7 C6 -177.5(5) . . . . ?
C1 C2 C7 C8 4.7(8) . . . . ?
C1 C10 C11 C12 15.8(6) . . . . ?
C2 C1 C10 C9 4.5(8) . . . . ?
C2 C1 C10 C11 -174.2(5) . . . . ?
C2 C3 C4 C5 -2.3(9) . . . . ?
C2 C7 C8 C9 0.5(9) . . . . ?
C3 C2 C7 C6 3.3(8) . . . . ?
C3 C2 C7 C8 -174.5(6) . . . . ?
C3 C4 C5 C6 2.8(10) . . . . ?
C4 C5 C6 C7 -0.1(10) . . . . ?
C5 C6 C7 C2 -2.9(9) . . . . ?
C5 C6 C7 C8 174.9(6) . . . . ?
C6 C7 C8 C9 -177.2(6) . . . . ?
C7 C2 C3 C4 -0.8(9) . . . . ?
C7 C8 C9 C10 -3.4(9) . . . . ?
C8 C9 C10 C1 1.0(8) . . . . ?
C8 C9 C10 C11 179.5(5) . . . . ?
C9 C10 C11 C12 -162.8(5) . . . . ?
C10 C1 C2 C3 171.9(6) . . . . ?
C10 C1 C2 C7 -7.3(8) . . . . ?
C10 C11 C12 N1 -27.1(5) . . . . ?
C10 C11 C12 C13 93.0(5) . . . . ?
C11 C12 C13 C14 -110.7(6) . . . . ?
C11 C12 C13 C18 68.0(6) . . . . ?
C12 N1 C1 C2 156.0(5) . . . . ?
C12 N1 C1 C10 -20.2(6) . . . . ?
C12 C13 C14 C15 177.6(5) . . . . ?
C12 C13 C18 C17 -178.1(5) . . . . ?
C13 C14 C15 C16 1.0(10) . . . . ?
C14 C13 C18 C17 0.7(8) . . . . ?
C14 C15 C16 C17 -0.4(10) . . . . ?
C15 C16 C17 C18 -0.1(10) . . . . ?
C16 C17 C18 C13 -0.1(9) . . . . ?
C18 C13 C14 C15 -1.1(8) . . . . ?
C19 S1 N1 C1 -50.2(5) . . . . ?
C19 S1 N1 C12 73.4(4) . . . . ?
C19 C20 C21 C22 -1.0(9) . . . . ?
C20 C19 C24 C23 -2.0(9) . . . . ?
C20 C21 C22 Br1 178.7(4) . . . . ?
C20 C21 C22 C23 0.1(10) . . . . ?
C21 C22 C23 C24 -0.1(9) . . . . ?
C22 C23 C24 C19 1.1(9) . . . . ?
C24 C19 C20 C21 1.9(8) . . . . ?

_olex2_date_sample_data_collection 2017-05-03
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_liuce_1114_2
_database_code_depnum_ccdc_archive 'CCDC 1815733'
_audit_update_record             
;
2018-01-09 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2016-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        6-nitro-1-tosylindoline
_chemical_formula_moiety         'C15 H14 N2 O4 S'
_chemical_formula_sum            'C15 H14 N2 O4 S'
_chemical_formula_weight         318.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7131(9)
_cell_length_b                   7.8152(8)
_cell_length_c                   21.654(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.171(9)
_cell_angle_gamma                90.00
_cell_volume                     1473.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    903
_cell_measurement_temperature    291.37(10)
_cell_measurement_theta_max      23.6470
_cell_measurement_theta_min      3.7610
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5031
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.50
_diffrn_ambient_temperature      291.37(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -96.00  -66.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  178.0000   30.0000 15

#__ type_ start__ end____ width___ exp.time_
  2 omega  -47.00   67.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -19.0000   90.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega  -29.00   45.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -57.0000    0.0000 37
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0695876000
_diffrn_orient_matrix_UB_12      0.0461295000
_diffrn_orient_matrix_UB_13      -0.0022016000
_diffrn_orient_matrix_UB_21      0.0306007000
_diffrn_orient_matrix_UB_22      -0.0671933000
_diffrn_orient_matrix_UB_23      -0.0178364000
_diffrn_orient_matrix_UB_31      -0.0291732000
_diffrn_orient_matrix_UB_32      0.0399310000
_diffrn_orient_matrix_UB_33      -0.0274301000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1801
_reflns_number_total             2900
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0382P)²+0.1656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1406
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C11(H11), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.09020(9) 0.66016(13) 0.13176(4) 0.0540(3) Uani 1 d . . .
O1 O 0.3840(5) 0.9441(4) -0.05823(16) 0.1426(16) Uani 1 d . . .
O2 O 0.5099(3) 0.7890(4) -0.11796(12) 0.0811(8) Uani 1 d . . .
O3 O 0.0645(3) 0.8192(3) 0.10018(10) 0.0620(7) Uani 1 d . . .
O4 O -0.0216(2) 0.5932(4) 0.17163(10) 0.0753(8) Uani 1 d . . .
N1 N 0.1107(3) 0.5132(3) 0.07874(10) 0.0481(7) Uani 1 d . . .
N2 N 0.4203(3) 0.8070(4) -0.07710(13) 0.0602(8) Uani 1 d . . .
C1 C 0.2055(3) 0.5300(4) 0.02716(12) 0.0392(7) Uani 1 d . . .
C2 C 0.2637(3) 0.6755(4) 0.00192(13) 0.0436(7) Uani 1 d . . .
H2 H 0.2454 0.7832 0.0184 0.052 Uiso 1 calc . . R
C3 C 0.3518(3) 0.6535(4) -0.04959(13) 0.0420(7) Uani 1 d . . .
C4 C 0.3791(3) 0.4982(4) -0.07595(13) 0.0491(8) Uani 1 d . . .
H4 H 0.4379 0.4896 -0.1108 0.059 Uiso 1 calc . . R
C5 C 0.3173(4) 0.3546(4) -0.04957(14) 0.0523(8) Uani 1 d . . .
H5 H 0.3337 0.2475 -0.0668 0.063 Uiso 1 calc . . R
C6 C 0.2319(3) 0.3691(4) 0.00205(13) 0.0438(7) Uani 1 d . . .
C7 C 0.1512(4) 0.2348(4) 0.03778(14) 0.0557(9) Uani 1 d . . .
H7A H 0.2197 0.1405 0.0484 0.067 Uiso 1 calc . . R
H7B H 0.0625 0.1910 0.0144 0.067 Uiso 1 calc . . R
C8 C 0.1030(4) 0.3289(5) 0.09540(15) 0.0631(10) Uani 1 d . . .
H8A H -0.0005 0.2971 0.1058 0.076 Uiso 1 calc . . R
H8B H 0.1724 0.3033 0.1303 0.076 Uiso 1 calc . . R
C9 C 0.2994(4) 0.5615(5) 0.22113(15) 0.0629(10) Uani 1 d . . .
H9 H 0.2288 0.4775 0.2310 0.075 Uiso 1 calc . . R
C10 C 0.2661(3) 0.6758(4) 0.17356(12) 0.0445(8) Uani 1 d . . .
C11 C 0.3710(3) 0.7989(4) 0.15944(13) 0.0454(8) Uani 1 d . . .
H11 H 0.3494 0.8754 0.1274 0.054 Uiso 1 calc . . R
C12 C 0.5080(3) 0.8093(4) 0.19261(14) 0.0489(8) Uani 1 d . . .
H12 H 0.5778 0.8942 0.1828 0.059 Uiso 1 calc . . R
C13 C 0.5453(3) 0.6964(4) 0.24042(14) 0.0475(8) Uani 1 d . . .
C14 C 0.4386(4) 0.5738(5) 0.25374(15) 0.0637(10) Uani 1 d . . .
H14 H 0.4605 0.4967 0.2856 0.076 Uiso 1 calc . . R
C15 C 0.6954(4) 0.7104(5) 0.27689(16) 0.0665(10) Uani 1 d . . .
H15A H 0.7789 0.6946 0.2498 0.100 Uiso 1 calc . . GR
H15B H 0.6999 0.6240 0.3084 0.100 Uiso 1 calc . . GR
H15C H 0.7031 0.8214 0.2957 0.100 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.432(2) . ?
S1 O4 1.425(2) . ?
S1 N1 1.639(3) . ?
S1 C10 1.754(3) . ?
O1 N2 1.193(4) . ?
O2 N2 1.210(3) . ?
N1 C1 1.420(3) . ?
N1 C8 1.487(4) . ?
N2 C3 1.476(4) . ?
C1 C2 1.368(4) . ?
C1 C6 1.392(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(4) . ?
C3 C4 1.366(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(4) . ?
C6 C7 1.495(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.521(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.385(4) . ?
C9 C14 1.383(4) . ?
C10 C11 1.370(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(4) . ?
C13 C14 1.374(4) . ?
C13 C15 1.506(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N1 107.05(13) . . ?
O3 S1 C10 107.68(15) . . ?
O4 S1 O3 120.66(15) . . ?
O4 S1 N1 105.20(15) . . ?
O4 S1 C10 108.45(14) . . ?
N1 S1 C10 107.10(13) . . ?
C1 N1 S1 124.6(2) . . ?
C1 N1 C8 108.3(2) . . ?
C8 N1 S1 120.1(2) . . ?
O1 N2 O2 122.8(3) . . ?
O1 N2 C3 118.3(3) . . ?
O2 N2 C3 118.9(3) . . ?
C2 C1 N1 128.8(3) . . ?
C2 C1 C6 121.7(3) . . ?
C6 C1 N1 109.5(3) . . ?
C1 C2 H2 121.9 . . ?
C1 C2 C3 116.3(3) . . ?
C3 C2 H2 121.9 . . ?
C2 C3 N2 117.9(3) . . ?
C4 C3 N2 118.3(3) . . ?
C4 C3 C2 123.8(3) . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.3(3) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 110.1(3) . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C7 130.1(3) . . ?
C6 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
C6 C7 C8 103.6(3) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
N1 C8 C7 104.6(3) . . ?
N1 C8 H8A 110.8 . . ?
N1 C8 H8B 110.8 . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 H9 120.3 . . ?
C14 C9 H9 120.3 . . ?
C14 C9 C10 119.3(3) . . ?
C9 C10 S1 119.5(2) . . ?
C11 C10 S1 120.7(2) . . ?
C11 C10 C9 119.7(3) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.8(3) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C15 121.2(3) . . ?
C14 C13 C12 117.3(3) . . ?
C14 C13 C15 121.4(3) . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.9(3) . . ?
C13 C14 H14 119.1 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 -18.7(4) . . . . ?
S1 N1 C1 C6 162.9(2) . . . . ?
S1 N1 C8 C7 -171.5(2) . . . . ?
S1 C10 C11 C12 180.0(2) . . . . ?
O1 N2 C3 C2 -7.9(5) . . . . ?
O1 N2 C3 C4 172.4(3) . . . . ?
O2 N2 C3 C2 172.5(3) . . . . ?
O2 N2 C3 C4 -7.1(4) . . . . ?
O3 S1 N1 C1 46.9(3) . . . . ?
O3 S1 N1 C8 -165.8(2) . . . . ?
O3 S1 C10 C9 162.1(3) . . . . ?
O3 S1 C10 C11 -18.2(3) . . . . ?
O4 S1 N1 C1 176.4(2) . . . . ?
O4 S1 N1 C8 -36.3(3) . . . . ?
O4 S1 C10 C9 30.0(3) . . . . ?
O4 S1 C10 C11 -150.3(3) . . . . ?
N1 S1 C10 C9 -83.0(3) . . . . ?
N1 S1 C10 C11 96.6(3) . . . . ?
N1 C1 C2 C3 -178.9(2) . . . . ?
N1 C1 C6 C5 178.1(2) . . . . ?
N1 C1 C6 C7 0.2(3) . . . . ?
N2 C3 C4 C5 178.9(3) . . . . ?
C1 N1 C8 C7 -19.4(3) . . . . ?
C1 C2 C3 N2 -178.3(3) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C1 C6 C7 C8 -12.1(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C1 C6 C7 -178.4(3) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C4 C5 C6 C7 178.5(3) . . . . ?
C5 C6 C7 C8 170.3(3) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C6 C7 C8 N1 18.6(3) . . . . ?
C8 N1 C1 C2 -169.2(3) . . . . ?
C8 N1 C1 C6 12.4(3) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 S1 N1 C1 -68.3(3) . . . . ?
C10 S1 N1 C8 78.9(3) . . . . ?
C10 C9 C14 C13 0.1(5) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
C11 C12 C13 C15 -179.4(3) . . . . ?
C12 C13 C14 C9 0.1(5) . . . . ?
C14 C9 C10 S1 179.6(3) . . . . ?
C14 C9 C10 C11 0.0(5) . . . . ?
C15 C13 C14 C9 179.0(3) . . . . ?

_olex2_date_sample_data_collection 2016-11-14
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_liuc_0308_2
_database_code_depnum_ccdc_archive 'CCDC 1815737'
_audit_update_record             
;
2018-01-09 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2017-03-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H25 N3 O2 Pd S'
_chemical_formula_sum            'C28 H25 N3 O2 Pd S'
_chemical_formula_weight         573.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Pd S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1719(16)
_cell_length_b                   9.5500(11)
_cell_length_c                   15.502(3)
_cell_angle_alpha                87.411(13)
_cell_angle_beta                 88.915(16)
_cell_angle_gamma                80.386(13)
_cell_volume                     1191.5(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1289
_cell_measurement_temperature    291.17(10)
_cell_measurement_theta_max      23.1390
_cell_measurement_theta_min      3.7960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.1214
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7926
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.336
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.17(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   19.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  150.0000 16

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   89.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000   30.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   93.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega   74.00  102.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -150.0000 14

#__ type_ start__ end____ width___ exp.time_
  5 omega  -45.00   47.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
  6 omega  -12.00   16.00   2.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000    0.0000 14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0570614000
_diffrn_orient_matrix_UB_12      0.0181353000
_diffrn_orient_matrix_UB_13      -0.0342313000
_diffrn_orient_matrix_UB_21      -0.0670194000
_diffrn_orient_matrix_UB_22      0.0030052000
_diffrn_orient_matrix_UB_23      0.0299805000
_diffrn_orient_matrix_UB_31      0.0018054000
_diffrn_orient_matrix_UB_32      0.0731232000
_diffrn_orient_matrix_UB_33      0.0052438000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3328
_reflns_number_total             4671
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0191P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.15692(6) 0.20529(4) 0.66150(3) 0.02088(14) Uani 1 1 d . . . . .
S1 S 0.29928(19) 0.45256(14) 0.74622(9) 0.0220(3) Uani 1 1 d . . . . .
O1 O 0.4449(5) 0.3741(4) 0.7050(2) 0.0274(10) Uani 1 1 d . . . . .
O2 O 0.2821(5) 0.6061(3) 0.7418(2) 0.0304(10) Uani 1 1 d . . . . .
N1 N 0.1406(6) 0.4033(4) 0.7071(3) 0.0195(11) Uani 1 1 d . . . . .
N2 N 0.1622(6) 0.0153(4) 0.6006(3) 0.0203(11) Uani 1 1 d . . . . .
N3 N 0.2725(6) 0.2521(4) 0.5409(3) 0.0179(10) Uani 1 1 d . . . . .
C1 C 0.0335(7) 0.1544(5) 0.7674(4) 0.0212(13) Uani 1 1 d . . . . .
C2 C 0.0777(8) 0.0340(6) 0.8220(4) 0.0275(15) Uani 1 1 d . . . . .
C3 C -0.0312(8) 0.0047(6) 0.8875(4) 0.0352(17) Uani 1 1 d . . . . .
H3 H -0.0024 -0.0764 0.9231 0.042 Uiso 1 1 calc R . . . .
C4 C -0.1799(8) 0.0917(6) 0.9015(4) 0.0411(18) Uani 1 1 d . . . . .
H4 H -0.2518 0.0689 0.9451 0.049 Uiso 1 1 calc R . . . .
C5 C -0.2211(8) 0.2134(6) 0.8498(4) 0.0349(16) Uani 1 1 d . . . . .
H5 H -0.3213 0.2733 0.8591 0.042 Uiso 1 1 calc R . . . .
C6 C -0.1145(7) 0.2478(6) 0.7838(4) 0.0248(14) Uani 1 1 d . . . . .
C7 C -0.1523(7) 0.3871(5) 0.7329(4) 0.0259(14) Uani 1 1 d . . . . .
H7A H -0.2577 0.4392 0.7523 0.031 Uiso 1 1 calc R . . . .
H7B H -0.1617 0.3691 0.6723 0.031 Uiso 1 1 calc R . . . .
C8 C -0.0180(7) 0.4755(5) 0.7438(4) 0.0265(14) Uani 1 1 d . . . . .
H8A H -0.0495 0.5679 0.7147 0.032 Uiso 1 1 calc R . . . .
H8B H -0.0046 0.4898 0.8046 0.032 Uiso 1 1 calc R . . . .
C9 C 0.3089(7) 0.4040(6) 0.8585(4) 0.0229(14) Uani 1 1 d . . . . .
C10 C 0.3533(7) 0.2625(6) 0.8844(4) 0.0260(14) Uani 1 1 d . . . . .
H10 H 0.3788 0.1944 0.8430 0.031 Uiso 1 1 calc R . . . .
C11 C 0.3603(8) 0.2213(6) 0.9708(4) 0.0313(15) Uani 1 1 d . . . . .
H11 H 0.3923 0.1258 0.9869 0.038 Uiso 1 1 calc R . . . .
C12 C 0.3209(8) 0.3185(7) 1.0334(4) 0.0367(17) Uani 1 1 d . . . . .
C13 C 0.2714(10) 0.4605(7) 1.0068(4) 0.052(2) Uani 1 1 d . . . . .
H13 H 0.2415 0.5282 1.0481 0.063 Uiso 1 1 calc R . . . .
C14 C 0.2662(9) 0.5027(6) 0.9200(4) 0.046(2) Uani 1 1 d . . . . .
H14 H 0.2336 0.5980 0.9035 0.055 Uiso 1 1 calc R . . . .
C15 C 0.3292(10) 0.2757(7) 1.1280(4) 0.058(2) Uani 1 1 d . . . . .
H15A H 0.2191 0.2880 1.1522 0.086 Uiso 1 1 calc GR . . . .
H15B H 0.3940 0.3340 1.1570 0.086 Uiso 1 1 calc GR . . . .
H15C H 0.3800 0.1778 1.1351 0.086 Uiso 1 1 calc GR . . . .
C16 C 0.2460(8) -0.0592(5) 0.8162(4) 0.0322(16) Uani 1 1 d . . . . .
H16A H 0.3084 -0.0249 0.7690 0.048 Uiso 1 1 calc GR . . . .
H16B H 0.2320 -0.1551 0.8068 0.048 Uiso 1 1 calc GR . . . .
H16C H 0.3045 -0.0567 0.8691 0.048 Uiso 1 1 calc GR . . . .
C17 C 0.1001(7) -0.0976(5) 0.6287(4) 0.0242(14) Uani 1 1 d . . . . .
H17 H 0.0474 -0.0959 0.6825 0.029 Uiso 1 1 calc R . . . .
C18 C 0.1103(8) -0.2201(6) 0.5807(4) 0.0278(15) Uani 1 1 d . . . . .
H18 H 0.0664 -0.2982 0.6029 0.033 Uiso 1 1 calc R . . . .
C19 C 0.1850(8) -0.2234(5) 0.5018(4) 0.0283(15) Uani 1 1 d . . . . .
H19 H 0.1929 -0.3043 0.4698 0.034 Uiso 1 1 calc R . . . .
C20 C 0.2502(7) -0.1049(5) 0.4684(4) 0.0211(13) Uani 1 1 d . . . . .
C21 C 0.3262(7) -0.0973(6) 0.3850(4) 0.0269(14) Uani 1 1 d . . . . .
H21 H 0.3389 -0.1764 0.3511 0.032 Uiso 1 1 calc R . . . .
C22 C 0.3804(7) 0.0220(6) 0.3539(4) 0.0277(15) Uani 1 1 d . . . . .
H22 H 0.4274 0.0240 0.2988 0.033 Uiso 1 1 calc R . . . .
C23 C 0.3661(7) 0.1451(5) 0.4048(4) 0.0210(13) Uani 1 1 d . . . . .
C24 C 0.4175(7) 0.2710(6) 0.3767(4) 0.0284(15) Uani 1 1 d . . . . .
H24 H 0.4674 0.2783 0.3226 0.034 Uiso 1 1 calc R . . . .
C25 C 0.3939(7) 0.3856(6) 0.4296(4) 0.0255(14) Uani 1 1 d . . . . .
H25 H 0.4265 0.4711 0.4115 0.031 Uiso 1 1 calc R . . . .
C26 C 0.3200(7) 0.3703(6) 0.5110(4) 0.0269(14) Uani 1 1 d . . . . .
H26 H 0.3035 0.4482 0.5459 0.032 Uiso 1 1 calc R . . . .
C27 C 0.2934(7) 0.1378(5) 0.4883(3) 0.0198(13) Uani 1 1 d . . . . .
C28 C 0.2356(7) 0.0130(5) 0.5210(4) 0.0186(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 N1 2.032(4) . ?
Pd1 N2 2.076(4) . ?
Pd1 N3 2.141(4) . ?
Pd1 C1 1.994(5) . ?
S1 O1 1.450(4) . ?
S1 O2 1.448(3) . ?
S1 N1 1.590(5) . ?
S1 C9 1.781(6) . ?
N1 C8 1.479(6) . ?
N2 C17 1.319(6) . ?
N2 C28 1.361(6) . ?
N3 C26 1.317(6) . ?
N3 C27 1.378(6) . ?
C1 C2 1.398(8) . ?
C1 C6 1.404(7) . ?
C2 C3 1.387(8) . ?
C2 C16 1.512(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(7) . ?
C6 C7 1.505(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.509(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.382(7) . ?
C9 C14 1.370(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(7) . ?
C12 C13 1.394(8) . ?
C12 C15 1.504(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(9) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.405(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.356(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.404(7) . ?
C20 C21 1.427(7) . ?
C20 C28 1.408(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.356(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.434(7) . ?
C23 C24 1.388(7) . ?
C23 C27 1.417(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.383(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.401(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.424(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Pd1 N2 172.91(18) . . ?
N1 Pd1 N3 95.85(16) . . ?
N2 Pd1 N3 79.27(16) . . ?
C1 Pd1 N1 87.53(18) . . ?
C1 Pd1 N2 96.96(19) . . ?
C1 Pd1 N3 174.6(2) . . ?
O1 S1 N1 107.6(2) . . ?
O1 S1 C9 107.6(3) . . ?
O2 S1 O1 117.0(2) . . ?
O2 S1 N1 110.5(2) . . ?
O2 S1 C9 105.0(2) . . ?
N1 S1 C9 108.8(2) . . ?
S1 N1 Pd1 120.2(2) . . ?
C8 N1 Pd1 120.1(3) . . ?
C8 N1 S1 113.4(3) . . ?
C17 N2 Pd1 128.0(4) . . ?
C17 N2 C28 118.2(4) . . ?
C28 N2 Pd1 113.8(3) . . ?
C26 N3 Pd1 130.2(4) . . ?
C26 N3 C27 118.0(5) . . ?
C27 N3 Pd1 111.8(3) . . ?
C2 C1 Pd1 126.0(4) . . ?
C2 C1 C6 119.2(5) . . ?
C6 C1 Pd1 114.7(4) . . ?
C1 C2 C16 121.9(5) . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 C16 118.8(6) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(6) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(6) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(6) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 119.6(5) . . ?
C5 C6 C1 119.6(6) . . ?
C5 C6 C7 120.7(5) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C6 C7 C8 111.1(5) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
N1 C8 C7 110.1(4) . . ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 S1 119.3(4) . . ?
C14 C9 S1 121.6(5) . . ?
C14 C9 C10 119.1(6) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(6) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 117.8(6) . . ?
C11 C12 C15 121.9(6) . . ?
C13 C12 C15 120.3(6) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(6) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C13 120.0(6) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17 118.7 . . ?
N2 C17 C18 122.6(5) . . ?
C18 C17 H17 118.7 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.3(5) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 124.0(5) . . ?
C19 C20 C28 116.7(5) . . ?
C28 C20 C21 119.3(5) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 C20 121.8(5) . . ?
C22 C21 H21 119.1 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.7(5) . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 123.8(5) . . ?
C24 C23 C27 118.4(5) . . ?
C27 C23 C22 117.9(5) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.5(5) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 120.7 . . ?
C24 C25 C26 118.6(5) . . ?
C26 C25 H25 120.7 . . ?
N3 C26 C25 123.8(5) . . ?
N3 C26 H26 118.1 . . ?
C25 C26 H26 118.1 . . ?
N3 C27 C23 121.6(5) . . ?
N3 C27 C28 116.8(5) . . ?
C23 C27 C28 121.5(5) . . ?
N2 C28 C20 122.9(5) . . ?
N2 C28 C27 118.3(4) . . ?
C20 C28 C27 118.7(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pd1 N1 C8 C7 -5.1(6) . . . . ?
Pd1 N2 C17 C18 179.3(4) . . . . ?
Pd1 N2 C28 C20 -179.1(4) . . . . ?
Pd1 N2 C28 C27 -2.0(6) . . . . ?
Pd1 N3 C26 C25 -179.6(4) . . . . ?
Pd1 N3 C27 C23 179.4(4) . . . . ?
Pd1 N3 C27 C28 0.6(6) . . . . ?
Pd1 C1 C2 C3 -172.5(4) . . . . ?
Pd1 C1 C2 C16 12.2(8) . . . . ?
Pd1 C1 C6 C5 172.2(5) . . . . ?
Pd1 C1 C6 C7 -10.8(7) . . . . ?
S1 N1 C8 C7 -157.3(4) . . . . ?
S1 C9 C10 C11 -179.4(5) . . . . ?
S1 C9 C14 C13 178.5(6) . . . . ?
O1 S1 N1 Pd1 27.8(3) . . . . ?
O1 S1 N1 C8 180.0(4) . . . . ?
O1 S1 C9 C10 -43.8(5) . . . . ?
O1 S1 C9 C14 139.1(5) . . . . ?
O2 S1 N1 Pd1 156.7(2) . . . . ?
O2 S1 N1 C8 -51.1(4) . . . . ?
O2 S1 C9 C10 -169.2(5) . . . . ?
O2 S1 C9 C14 13.7(6) . . . . ?
N1 S1 C9 C10 72.5(5) . . . . ?
N1 S1 C9 C14 -104.6(6) . . . . ?
N2 C17 C18 C19 -0.8(9) . . . . ?
N3 C27 C28 N2 1.0(8) . . . . ?
N3 C27 C28 C20 178.2(5) . . . . ?
C1 C2 C3 C4 -1.2(9) . . . . ?
C1 C6 C7 C8 -58.6(7) . . . . ?
C2 C1 C6 C5 -5.1(8) . . . . ?
C2 C1 C6 C7 171.9(5) . . . . ?
C2 C3 C4 C5 -1.2(10) . . . . ?
C3 C4 C5 C6 0.5(10) . . . . ?
C4 C5 C6 C1 2.7(9) . . . . ?
C4 C5 C6 C7 -174.3(6) . . . . ?
C5 C6 C7 C8 118.4(6) . . . . ?
C6 C1 C2 C3 4.4(8) . . . . ?
C6 C1 C2 C16 -170.9(5) . . . . ?
C6 C7 C8 N1 64.3(6) . . . . ?
C9 S1 N1 Pd1 -88.5(3) . . . . ?
C9 S1 N1 C8 63.7(4) . . . . ?
C9 C10 C11 C12 1.1(10) . . . . ?
C10 C9 C14 C13 1.4(10) . . . . ?
C10 C11 C12 C13 0.8(10) . . . . ?
C10 C11 C12 C15 -179.4(6) . . . . ?
C11 C12 C13 C14 -1.6(11) . . . . ?
C12 C13 C14 C9 0.5(12) . . . . ?
C14 C9 C10 C11 -2.2(9) . . . . ?
C15 C12 C13 C14 178.7(7) . . . . ?
C16 C2 C3 C4 174.2(6) . . . . ?
C17 N2 C28 C20 -1.0(8) . . . . ?
C17 N2 C28 C27 176.1(5) . . . . ?
C17 C18 C19 C20 -0.4(9) . . . . ?
C18 C19 C20 C21 -178.0(6) . . . . ?
C18 C19 C20 C28 0.9(9) . . . . ?
C19 C20 C21 C22 176.8(6) . . . . ?
C19 C20 C28 N2 -0.1(8) . . . . ?
C19 C20 C28 C27 -177.2(5) . . . . ?
C20 C21 C22 C23 1.3(9) . . . . ?
C21 C20 C28 N2 178.8(5) . . . . ?
C21 C20 C28 C27 1.7(8) . . . . ?
C21 C22 C23 C24 -179.3(6) . . . . ?
C21 C22 C23 C27 -0.2(8) . . . . ?
C22 C23 C24 C25 178.0(5) . . . . ?
C22 C23 C27 N3 -178.9(5) . . . . ?
C22 C23 C27 C28 -0.1(8) . . . . ?
C23 C24 C25 C26 0.7(9) . . . . ?
C23 C27 C28 N2 -177.9(5) . . . . ?
C23 C27 C28 C20 -0.7(8) . . . . ?
C24 C23 C27 N3 0.3(8) . . . . ?
C24 C23 C27 C28 179.1(5) . . . . ?
C24 C25 C26 N3 0.7(9) . . . . ?
C26 N3 C27 C23 1.0(8) . . . . ?
C26 N3 C27 C28 -177.9(5) . . . . ?
C27 N3 C26 C25 -1.5(9) . . . . ?
C27 C23 C24 C25 -1.1(9) . . . . ?
C28 N2 C17 C18 1.5(8) . . . . ?
C28 C20 C21 C22 -2.0(9) . . . . ?

_olex2_date_sample_data_collection 2017-03-08
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_liuc_0516
_database_code_depnum_ccdc_archive 'CCDC 1815740'
_audit_update_record             
;
2018-01-09 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2017-05-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_name_common            ?
_chemical_name_systematic        
(S)-1-((4-bromophenyl)sulfonyl)-3-phenyl-2,3-dihydro-1H-benzo[g]indole
_chemical_formula_moiety         'C24 H18 Br N O2 S'
_chemical_formula_sum            'C24 H18 Br N O2 S'
_chemical_formula_weight         464.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.0085(4)
_cell_length_b                   10.9667(7)
_cell_length_c                   26.5254(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2038.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1301
_cell_measurement_temperature    292.4(5)
_cell_measurement_theta_max      22.3390
_cell_measurement_theta_min      3.5850
_exptl_absorpt_coefficient_mu    2.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7932
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.29
_diffrn_ambient_temperature      292.4(5)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -8.00   25.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega   52.00   83.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  178.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega   61.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305 -178.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega  -24.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   19.0000  -30.0000 122
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0211698000
_diffrn_orient_matrix_UB_12      -0.0443596000
_diffrn_orient_matrix_UB_13      -0.0186511000
_diffrn_orient_matrix_UB_21      0.0001403000
_diffrn_orient_matrix_UB_22      -0.0461184000
_diffrn_orient_matrix_UB_23      0.0187312000
_diffrn_orient_matrix_UB_31      -0.0989879000
_diffrn_orient_matrix_UB_32      0.0093961000
_diffrn_orient_matrix_UB_33      0.0040083000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2529
_reflns_number_total             4020
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(11)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4020
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0277P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.1007
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.69128(9) 0.07606(8) 0.17121(2) 0.0830(3) Uani 1 d . . .
S1 S -0.06692(15) 0.06994(14) 0.30531(5) 0.0422(3) Uani 1 d . . .
O1 O -0.1836(4) 0.1722(3) 0.29279(12) 0.0547(10) Uani 1 d . . .
O2 O -0.1459(4) -0.0506(3) 0.30477(12) 0.0520(10) Uani 1 d . . .
N1 N 0.0134(4) 0.0964(4) 0.36366(13) 0.0375(10) Uani 1 d . . .
C1 C 0.1496(6) 0.0127(4) 0.38610(15) 0.0326(11) Uani 1 d . . .
C2 C 0.1152(6) -0.1070(4) 0.40350(16) 0.0334(12) Uani 1 d . . .
C3 C -0.0610(6) -0.1675(5) 0.40208(18) 0.0453(13) Uani 1 d . . .
H3 H -0.1654 -0.1284 0.3877 0.054 Uiso 1 calc . . R
C4 C -0.0834(8) -0.2813(5) 0.4210(2) 0.0554(15) Uani 1 d . . .
H4 H -0.2021 -0.3190 0.4196 0.066 Uiso 1 calc . . R
C5 C 0.0728(8) -0.3427(5) 0.44283(19) 0.0535(14) Uani 1 d . . .
H5 H 0.0579 -0.4212 0.4555 0.064 Uiso 1 calc . . R
C6 C 0.2445(7) -0.2866(5) 0.44521(17) 0.0461(14) Uani 1 d . . .
H6 H 0.3468 -0.3276 0.4598 0.055 Uiso 1 calc . . R
C7 C 0.2728(6) -0.1681(5) 0.42622(17) 0.0349(12) Uani 1 d . . .
C8 C 0.4514(6) -0.1095(5) 0.43015(18) 0.0409(13) Uani 1 d . . .
H8 H 0.5536 -0.1514 0.4443 0.049 Uiso 1 calc . . R
C9 C 0.4776(6) 0.0071(5) 0.41361(18) 0.0455(14) Uani 1 d . . .
H9 H 0.5961 0.0445 0.4165 0.055 Uiso 1 calc . . R
C10 C 0.3236(6) 0.0694(5) 0.39218(14) 0.0347(11) Uani 1 d . . .
C11 C 0.3170(6) 0.2013(5) 0.37422(17) 0.0401(12) Uani 1 d . . .
H11 H 0.3729 0.2066 0.3404 0.048 Uiso 1 calc . . R
C12 C 0.0988(6) 0.2206(5) 0.3706(2) 0.0509(14) Uani 1 d . . .
H12A H 0.0507 0.2582 0.4012 0.061 Uiso 1 calc . . R
H12B H 0.0678 0.2727 0.3423 0.061 Uiso 1 calc . . R
C13 C 0.4215(6) 0.2884(4) 0.40941(18) 0.0366(12) Uani 1 d . . .
C14 C 0.5951(6) 0.3342(5) 0.3944(2) 0.0491(14) Uani 1 d . . .
H14 H 0.6459 0.3124 0.3633 0.059 Uiso 1 calc . . R
C15 C 0.6940(7) 0.4131(5) 0.4258(2) 0.0564(15) Uani 1 d . . .
H15 H 0.8104 0.4448 0.4151 0.068 Uiso 1 calc . . R
C16 C 0.6250(7) 0.4453(6) 0.4717(2) 0.0539(15) Uani 1 d . . .
H16 H 0.6933 0.4980 0.4925 0.065 Uiso 1 calc . . R
C17 C 0.4519(7) 0.3986(5) 0.48718(18) 0.0557(15) Uani 1 d . . .
H17 H 0.4030 0.4193 0.5186 0.067 Uiso 1 calc . . R
C18 C 0.3516(7) 0.3212(5) 0.45601(18) 0.0522(15) Uani 1 d . . .
H18 H 0.2345 0.2906 0.4666 0.063 Uiso 1 calc . . R
C19 C 0.1359(5) 0.0692(5) 0.26582(16) 0.0378(11) Uani 1 d . . .
C20 C 0.1817(8) 0.1712(5) 0.23837(18) 0.0510(14) Uani 1 d . . .
H20 H 0.1013 0.2386 0.2391 0.061 Uiso 1 calc . . R
C21 C 0.3464(8) 0.1746(6) 0.20967(19) 0.0580(15) Uani 1 d . . .
H21 H 0.3774 0.2430 0.1907 0.070 Uiso 1 calc . . R
C22 C 0.4636(6) 0.0731(6) 0.21010(16) 0.0504(13) Uani 1 d . . .
C23 C 0.4210(7) -0.0308(6) 0.23658(18) 0.0562(16) Uani 1 d . . .
H23 H 0.5014 -0.0983 0.2357 0.067 Uiso 1 calc . . R
C24 C 0.2523(6) -0.0319(5) 0.26496(17) 0.0460(14) Uani 1 d . . .
H24 H 0.2189 -0.1011 0.2832 0.055 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C22 1.900(4) . ?
S1 O1 1.427(4) . ?
S1 O2 1.433(4) . ?
S1 N1 1.672(4) . ?
S1 C19 1.766(4) . ?
N1 C1 1.452(5) . ?
N1 C12 1.500(6) . ?
C1 C2 1.412(6) . ?
C1 C10 1.379(6) . ?
C2 C3 1.402(6) . ?
C2 C7 1.426(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.354(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.409(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.353(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.409(7) . ?
C7 C8 1.410(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.365(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(6) . ?
C10 C11 1.523(7) . ?
C11 H11 0.9800 . ?
C11 C12 1.547(6) . ?
C11 C13 1.524(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.375(6) . ?
C13 C18 1.378(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.359(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(7) . ?
C19 C24 1.377(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.383(8) . ?
C22 C23 1.372(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.402(7) . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.06(19) . . ?
O1 S1 N1 105.8(2) . . ?
O1 S1 C19 109.1(2) . . ?
O2 S1 N1 107.4(2) . . ?
O2 S1 C19 107.5(2) . . ?
N1 S1 C19 106.19(18) . . ?
C1 N1 S1 119.4(3) . . ?
C1 N1 C12 105.1(3) . . ?
C12 N1 S1 114.0(3) . . ?
C2 C1 N1 127.5(4) . . ?
C10 C1 N1 110.1(4) . . ?
C10 C1 C2 122.2(4) . . ?
C1 C2 C7 116.3(4) . . ?
C3 C2 C1 125.6(4) . . ?
C3 C2 C7 118.1(5) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.9(5) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(5) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.9(5) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C2 118.4(4) . . ?
C6 C7 C8 121.2(4) . . ?
C8 C7 C2 120.3(5) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.5(5) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.0(5) . . ?
C10 C9 H9 120.5 . . ?
C1 C10 C9 120.6(5) . . ?
C1 C10 C11 111.4(4) . . ?
C9 C10 C11 127.9(4) . . ?
C10 C11 H11 109.3 . . ?
C10 C11 C12 100.3(4) . . ?
C10 C11 C13 112.9(4) . . ?
C12 C11 H11 109.3 . . ?
C13 C11 H11 109.3 . . ?
C13 C11 C12 115.3(4) . . ?
N1 C12 C11 106.1(4) . . ?
N1 C12 H12A 110.5 . . ?
N1 C12 H12B 110.5 . . ?
C11 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C14 C13 C11 118.5(4) . . ?
C14 C13 C18 118.6(4) . . ?
C18 C13 C11 122.8(4) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.5(5) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 118.9(5) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0(5) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 121.2(5) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 S1 120.0(4) . . ?
C20 C19 C24 120.6(4) . . ?
C24 C19 S1 119.4(4) . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.6(5) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 121.0 . . ?
C22 C21 C20 118.0(5) . . ?
C22 C21 H21 121.0 . . ?
C21 C22 Br1 118.7(5) . . ?
C23 C22 Br1 118.3(5) . . ?
C23 C22 C21 122.9(5) . . ?
C22 C23 H23 121.1 . . ?
C22 C23 C24 117.8(5) . . ?
C24 C23 H23 121.1 . . ?
C19 C24 C23 120.1(5) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C22 C23 C24 -179.8(4) . . . . ?
S1 N1 C1 C2 -71.9(5) . . . . ?
S1 N1 C1 C10 112.7(3) . . . . ?
S1 N1 C12 C11 -106.8(4) . . . . ?
S1 C19 C20 C21 176.0(4) . . . . ?
S1 C19 C24 C23 -175.5(4) . . . . ?
O1 S1 N1 C1 -175.2(3) . . . . ?
O1 S1 N1 C12 -49.9(3) . . . . ?
O1 S1 C19 C20 14.5(4) . . . . ?
O1 S1 C19 C24 -168.9(4) . . . . ?
O2 S1 N1 C1 55.4(4) . . . . ?
O2 S1 N1 C12 -179.2(3) . . . . ?
O2 S1 C19 C20 146.1(4) . . . . ?
O2 S1 C19 C24 -37.2(4) . . . . ?
N1 S1 C19 C20 -99.1(4) . . . . ?
N1 S1 C19 C24 77.5(4) . . . . ?
N1 C1 C2 C3 0.1(7) . . . . ?
N1 C1 C2 C7 -177.2(4) . . . . ?
N1 C1 C10 C9 179.4(4) . . . . ?
N1 C1 C10 C11 0.7(5) . . . . ?
C1 N1 C12 C11 25.8(5) . . . . ?
C1 C2 C3 C4 -177.9(5) . . . . ?
C1 C2 C7 C6 178.6(4) . . . . ?
C1 C2 C7 C8 -0.3(6) . . . . ?
C1 C10 C11 C12 14.8(5) . . . . ?
C1 C10 C11 C13 138.1(4) . . . . ?
C2 C1 C10 C9 3.6(6) . . . . ?
C2 C1 C10 C11 -175.0(4) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C2 C7 C8 C9 1.5(7) . . . . ?
C3 C2 C7 C6 1.1(6) . . . . ?
C3 C2 C7 C8 -177.8(4) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C4 C5 C6 C7 -0.3(8) . . . . ?
C5 C6 C7 C2 -0.6(7) . . . . ?
C5 C6 C7 C8 178.3(5) . . . . ?
C6 C7 C8 C9 -177.4(5) . . . . ?
C7 C2 C3 C4 -0.7(7) . . . . ?
C7 C8 C9 C10 -0.2(7) . . . . ?
C8 C9 C10 C1 -2.4(7) . . . . ?
C8 C9 C10 C11 176.0(4) . . . . ?
C9 C10 C11 C12 -163.7(4) . . . . ?
C9 C10 C11 C13 -40.5(6) . . . . ?
C10 C1 C2 C3 175.1(4) . . . . ?
C10 C1 C2 C7 -2.2(6) . . . . ?
C10 C11 C12 N1 -24.3(5) . . . . ?
C10 C11 C13 C14 106.1(5) . . . . ?
C10 C11 C13 C18 -72.5(6) . . . . ?
C11 C13 C14 C15 -179.6(5) . . . . ?
C11 C13 C18 C17 178.8(5) . . . . ?
C12 N1 C1 C2 158.7(4) . . . . ?
C12 N1 C1 C10 -16.8(5) . . . . ?
C12 C11 C13 C14 -139.4(5) . . . . ?
C12 C11 C13 C18 42.1(7) . . . . ?
C13 C11 C12 N1 -145.9(4) . . . . ?
C13 C14 C15 C16 1.0(8) . . . . ?
C14 C13 C18 C17 0.2(8) . . . . ?
C14 C15 C16 C17 -0.4(9) . . . . ?
C15 C16 C17 C18 -0.4(8) . . . . ?
C16 C17 C18 C13 0.4(8) . . . . ?
C18 C13 C14 C15 -0.9(8) . . . . ?
C19 S1 N1 C1 -59.4(4) . . . . ?
C19 S1 N1 C12 66.0(4) . . . . ?
C19 C20 C21 C22 -0.8(8) . . . . ?
C20 C19 C24 C23 1.1(7) . . . . ?
C20 C21 C22 Br1 -179.7(4) . . . . ?
C20 C21 C22 C23 1.7(8) . . . . ?
C21 C22 C23 C24 -1.1(8) . . . . ?
C22 C23 C24 C19 -0.3(7) . . . . ?
C24 C19 C20 C21 -0.5(7) . . . . ?

_olex2_date_sample_data_collection 2017-05-17
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_liuc_0831-sr
_database_code_depnum_ccdc_archive 'CCDC 1815734'
_audit_update_record             
;
2018-01-09 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2016-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        
4-methyl-2-nitro-5-tosyl-5,5a,6,10b-tetrahydroindeno[2,1-b]indole
_chemical_formula_moiety         'C23 H20 N2 O4 S'
_chemical_formula_sum            'C23 H20 N2 O4 S'
_chemical_formula_weight         420.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0329(9)
_cell_length_b                   24.1681(14)
_cell_length_c                   8.5244(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.965(7)
_cell_angle_gamma                90
_cell_volume                     2405.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0969
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4738
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.372
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2135
_reflns_number_total             4738
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0621
_refine_ls_restrained_S_all      0.902
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1645
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C15(H15), C18(H18), C19(H19),
 C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.69638(8) 0.16599(4) 0.85298(9) 0.0597(3) Uani 1 1 d . . . . .
O1 O 0.7584(3) -0.08170(13) 0.4453(4) 0.1354(14) Uani 1 1 d . . . . .
O2 O 0.7294(3) -0.03236(13) 0.2362(4) 0.1403(16) Uani 1 1 d . . . . .
O3 O 0.7287(2) 0.12339(10) 0.9725(2) 0.0726(7) Uani 1 1 d . . . . .
O4 O 0.6524(2) 0.21757(9) 0.8943(2) 0.0740(7) Uani 1 1 d . . . . .
N1 N 0.7259(3) -0.03931(15) 0.3737(5) 0.0910(11) Uani 1 1 d . . . . .
N5 N 0.5937(2) 0.13986(10) 0.7044(2) 0.0524(7) Uani 1 1 d . . . . .
C1 C 0.5521(3) 0.17974(13) 0.5659(3) 0.0556(9) Uani 1 1 d . . . . .
H1 H 0.5840 0.2167 0.5948 0.067 Uiso 1 1 calc R . . . .
C2 C 0.4202(3) 0.18231(16) 0.5153(3) 0.0715(11) Uani 1 1 d . . . . .
H2A H 0.3866 0.1547 0.5725 0.086 Uiso 1 1 calc R . . . .
H2B H 0.3928 0.2186 0.5369 0.086 Uiso 1 1 calc R . . . .
C3 C 0.3917(3) 0.17062(14) 0.3377(4) 0.0602(9) Uani 1 1 d . . . . .
C4 C 0.2846(4) 0.17024(17) 0.2303(5) 0.0885(13) Uani 1 1 d . . . . .
H4 H 0.2192 0.1780 0.2662 0.106 Uiso 1 1 calc R . . . .
C5 C 0.2763(4) 0.15825(18) 0.0706(5) 0.0973(14) Uani 1 1 d . . . . .
H5 H 0.2049 0.1581 -0.0019 0.117 Uiso 1 1 calc R . . . .
C6 C 0.3711(5) 0.14662(17) 0.0173(5) 0.0994(15) Uani 1 1 d . . . . .
H6 H 0.3635 0.1388 -0.0916 0.119 Uiso 1 1 calc R . . . .
C7 C 0.4777(4) 0.14610(15) 0.1205(4) 0.0823(13) Uani 1 1 d . . . . .
H7 H 0.5422 0.1379 0.0829 0.099 Uiso 1 1 calc R . . . .
C8 C 0.4875(3) 0.15815(12) 0.2841(3) 0.0558(9) Uani 1 1 d . . . . .
C9 C 0.5939(3) 0.15648(12) 0.4210(3) 0.0516(8) Uani 1 1 d . . . . .
H9 H 0.6569 0.1781 0.3979 0.062 Uiso 1 1 calc R . . . .
C10 C 0.6291(3) 0.09819(12) 0.4737(3) 0.0481(8) Uani 1 1 d . . . . .
C11 C 0.6194(3) 0.08876(12) 0.6314(3) 0.0492(8) Uani 1 1 d . . . . .
C12 C 0.6283(3) 0.03655(13) 0.6995(3) 0.0567(9) Uani 1 1 d . . . . .
C13 C 0.6641(3) -0.00529(13) 0.6115(4) 0.0647(10) Uani 1 1 d . . . . .
H13 H 0.6750 -0.0409 0.6538 0.078 Uiso 1 1 calc R . . . .
C14 C 0.6835(3) 0.00568(14) 0.4619(4) 0.0617(9) Uani 1 1 d . . . . .
C15 C 0.6628(3) 0.05627(14) 0.3867(4) 0.0576(9) Uani 1 1 d . . . . .
H15 H 0.6713 0.0618 0.2822 0.069 Uiso 1 1 calc R . . . .
C16 C 0.5974(4) 0.02188(15) 0.8579(4) 0.0819(12) Uani 1 1 d . . . . .
H16A H 0.6659 0.0198 0.9431 0.123 Uiso 1 1 calc GR . . . .
H16B H 0.5590 -0.0132 0.8469 0.123 Uiso 1 1 calc GR . . . .
H16C H 0.5478 0.0498 0.8833 0.123 Uiso 1 1 calc GR . . . .
C17 C 0.8149(3) 0.17902(13) 0.7721(3) 0.0542(8) Uani 1 1 d . . . . .
C18 C 0.8349(3) 0.23141(14) 0.7186(3) 0.0628(9) Uani 1 1 d . . . . .
H18 H 0.7856 0.2604 0.7260 0.075 Uiso 1 1 calc R . . . .
C19 C 0.9278(3) 0.24035(15) 0.6544(4) 0.0691(10) Uani 1 1 d . . . . .
H19 H 0.9419 0.2757 0.6209 0.083 Uiso 1 1 calc R . . . .
C20 C 1.0000(3) 0.19791(18) 0.6392(4) 0.0699(10) Uani 1 1 d . . . . .
C21 C 0.9806(3) 0.14588(16) 0.6925(4) 0.0758(11) Uani 1 1 d . . . . .
H21 H 1.0302 0.1171 0.6845 0.091 Uiso 1 1 calc R . . . .
C22 C 0.8881(3) 0.13623(15) 0.7577(4) 0.0691(10) Uani 1 1 d . . . . .
H22 H 0.8749 0.1009 0.7922 0.083 Uiso 1 1 calc R . . . .
C23 C 1.1031(4) 0.20827(19) 0.5656(5) 0.1079(15) Uani 1 1 d . . . . .
H23A H 1.0856 0.2380 0.4890 0.162 Uiso 1 1 calc GR . . . .
H23B H 1.1191 0.1753 0.5120 0.162 Uiso 1 1 calc GR . . . .
H23C H 1.1688 0.2179 0.6499 0.162 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.434(2) . ?
S1 O4 1.431(2) . ?
S1 N5 1.666(2) . ?
S1 C17 1.756(3) . ?
O1 N1 1.208(4) . ?
O2 N1 1.195(4) . ?
N1 C14 1.481(4) . ?
N5 C1 1.513(4) . ?
N5 C11 1.450(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.542(5) . ?
C1 C9 1.547(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.497(4) . ?
C3 C4 1.389(5) . ?
C3 C8 1.373(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.355(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.401(4) . ?
C8 C9 1.510(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.508(4) . ?
C10 C11 1.396(4) . ?
C10 C15 1.373(4) . ?
C11 C12 1.382(4) . ?
C12 C13 1.388(4) . ?
C12 C16 1.526(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(4) . ?
C14 C15 1.375(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.387(4) . ?
C17 C22 1.383(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(5) . ?
C20 C21 1.376(5) . ?
C20 C23 1.539(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(5) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N5 106.99(13) . . ?
O3 S1 C17 107.50(15) . . ?
O4 S1 O3 120.23(13) . . ?
O4 S1 N5 105.49(14) . . ?
O4 S1 C17 108.89(15) . . ?
N5 S1 C17 107.06(12) . . ?
O1 N1 C14 118.3(3) . . ?
O2 N1 O1 122.1(4) . . ?
O2 N1 C14 119.5(4) . . ?
C1 N5 S1 113.4(2) . . ?
C11 N5 S1 116.9(2) . . ?
C11 N5 C1 105.8(2) . . ?
N5 C1 H1 110.4 . . ?
N5 C1 C2 111.6(3) . . ?
N5 C1 C9 106.4(2) . . ?
C2 C1 H1 110.4 . . ?
C2 C1 C9 107.6(2) . . ?
C9 C1 H1 110.4 . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.1(3) . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C4 C3 C2 128.2(3) . . ?
C8 C3 C2 111.9(3) . . ?
C8 C3 C4 120.0(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.3(4) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C8 118.6(4) . . ?
C8 C7 H7 120.7 . . ?
C3 C8 C7 120.1(3) . . ?
C3 C8 C9 111.8(3) . . ?
C7 C8 C9 128.0(3) . . ?
C1 C9 H9 112.5 . . ?
C8 C9 C1 103.3(3) . . ?
C8 C9 H9 112.5 . . ?
C10 C9 C1 102.9(2) . . ?
C10 C9 C8 112.3(2) . . ?
C10 C9 H9 112.5 . . ?
C11 C10 C9 110.9(3) . . ?
C15 C10 C9 128.8(3) . . ?
C15 C10 C11 120.3(3) . . ?
C10 C11 N5 110.5(3) . . ?
C12 C11 N5 126.9(3) . . ?
C12 C11 C10 122.5(3) . . ?
C11 C12 C13 116.2(3) . . ?
C11 C12 C16 124.9(3) . . ?
C13 C12 C16 118.8(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 N1 119.0(3) . . ?
C13 C14 C15 123.5(3) . . ?
C15 C14 N1 117.5(3) . . ?
C10 C15 C14 116.6(3) . . ?
C10 C15 H15 121.7 . . ?
C14 C15 H15 121.7 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 S1 121.0(3) . . ?
C22 C17 S1 119.7(3) . . ?
C22 C17 C18 119.3(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 C23 120.6(4) . . ?
C21 C20 C23 120.1(4) . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N5 C1 C2 -132.4(2) . . . . ?
S1 N5 C1 C9 110.5(2) . . . . ?
S1 N5 C11 C10 -110.5(2) . . . . ?
S1 N5 C11 C12 72.6(4) . . . . ?
S1 C17 C18 C19 -179.4(2) . . . . ?
S1 C17 C22 C21 179.2(3) . . . . ?
O1 N1 C14 C13 -10.9(6) . . . . ?
O1 N1 C14 C15 170.7(4) . . . . ?
O2 N1 C14 C13 170.6(4) . . . . ?
O2 N1 C14 C15 -7.7(6) . . . . ?
O3 S1 N5 C1 -178.62(19) . . . . ?
O3 S1 N5 C11 -55.0(2) . . . . ?
O3 S1 C17 C18 -148.3(2) . . . . ?
O3 S1 C17 C22 33.3(3) . . . . ?
O4 S1 N5 C1 52.3(2) . . . . ?
O4 S1 N5 C11 175.8(2) . . . . ?
O4 S1 C17 C18 -16.5(3) . . . . ?
O4 S1 C17 C22 165.0(2) . . . . ?
N1 C14 C15 C10 -176.8(3) . . . . ?
N5 S1 C17 C18 97.1(3) . . . . ?
N5 S1 C17 C22 -81.4(3) . . . . ?
N5 C1 C2 C3 -126.1(3) . . . . ?
N5 C1 C9 C8 131.2(2) . . . . ?
N5 C1 C9 C10 14.1(3) . . . . ?
N5 C11 C12 C13 -174.3(3) . . . . ?
N5 C11 C12 C16 8.2(5) . . . . ?
C1 N5 C11 C10 16.8(3) . . . . ?
C1 N5 C11 C12 -160.0(3) . . . . ?
C1 C2 C3 C4 -177.0(4) . . . . ?
C1 C2 C3 C8 4.2(4) . . . . ?
C1 C9 C10 C11 -4.3(3) . . . . ?
C1 C9 C10 C15 173.2(3) . . . . ?
C2 C1 C9 C8 11.4(3) . . . . ?
C2 C1 C9 C10 -105.6(3) . . . . ?
C2 C3 C4 C5 -179.8(4) . . . . ?
C2 C3 C8 C7 -179.9(3) . . . . ?
C2 C3 C8 C9 3.3(4) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C3 C8 C9 C1 -9.2(3) . . . . ?
C3 C8 C9 C10 101.0(3) . . . . ?
C4 C3 C8 C7 1.3(5) . . . . ?
C4 C3 C8 C9 -175.6(3) . . . . ?
C4 C5 C6 C7 0.4(7) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C6 C7 C8 C3 -0.6(5) . . . . ?
C6 C7 C8 C9 175.7(3) . . . . ?
C7 C8 C9 C1 174.2(3) . . . . ?
C7 C8 C9 C10 -75.6(4) . . . . ?
C8 C3 C4 C5 -1.1(6) . . . . ?
C8 C9 C10 C11 -114.7(3) . . . . ?
C8 C9 C10 C15 62.8(4) . . . . ?
C9 C1 C2 C3 -9.8(4) . . . . ?
C9 C10 C11 N5 -7.8(3) . . . . ?
C9 C10 C11 C12 169.2(3) . . . . ?
C9 C10 C15 C14 -176.0(3) . . . . ?
C10 C11 C12 C13 9.2(5) . . . . ?
C10 C11 C12 C16 -168.3(3) . . . . ?
C11 N5 C1 C2 98.1(3) . . . . ?
C11 N5 C1 C9 -19.0(3) . . . . ?
C11 C10 C15 C14 1.3(5) . . . . ?
C11 C12 C13 C14 -3.0(5) . . . . ?
C12 C13 C14 N1 177.7(3) . . . . ?
C12 C13 C14 C15 -4.1(5) . . . . ?
C13 C14 C15 C10 4.9(5) . . . . ?
C15 C10 C11 N5 174.5(3) . . . . ?
C15 C10 C11 C12 -8.5(5) . . . . ?
C16 C12 C13 C14 174.6(3) . . . . ?
C17 S1 N5 C1 -63.6(2) . . . . ?
C17 S1 N5 C11 60.0(2) . . . . ?
C17 C18 C19 C20 1.4(5) . . . . ?
C18 C17 C22 C21 0.7(5) . . . . ?
C18 C19 C20 C21 -1.6(5) . . . . ?
C18 C19 C20 C23 179.4(3) . . . . ?
C19 C20 C21 C22 1.3(5) . . . . ?
C20 C21 C22 C17 -0.9(5) . . . . ?
C22 C17 C18 C19 -1.0(5) . . . . ?
C23 C20 C21 C22 -179.6(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.245 246.3 27.3 ?
2 0.000 0.500 -0.160 246.3 27.3 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_liuc_3
_database_code_depnum_ccdc_archive 'CCDC 1822354'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2018-02-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_formula_moiety         'C35 H35 N3 O2 Pd S, C3 H7 N O'
_chemical_formula_sum            'C38 H42 N4 O3 Pd S'
_chemical_formula_weight         741.26
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Pd 0.17446 3.99061 19.33190 15.50170 5.29537 0.60584 0.69866 7.98929 25.20520
76.89860 5.26593017578
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   10.2072(5)
_cell_length_b                   13.9301(10)
_cell_length_c                   15.1016(13)
_cell_angle_alpha                66.531(8)
_cell_angle_beta                 75.760(6)
_cell_angle_gamma                88.492(5)
_cell_volume                     1902.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7269
_cell_measurement_temperature    173
_cell_measurement_theta_max      69.6850
_cell_measurement_theta_min      4.8360
_exptl_absorpt_coefficient_mu    4.753
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2936
_exptl_crystal_description       block
_exptl_crystal_F_000             771.0106
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12232
_diffrn_reflns_theta_full        66.6009
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         4.84
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9644
_diffrn_measured_fraction_theta_max 0.9644
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -63.00  -37.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   60.0000 17

#__ type_ start__ end____ width___ exp.time_
  2 omega  -76.00  -34.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -33.00   10.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -78.00  -51.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000 -150.0000 18

#__ type_ start__ end____ width___ exp.time_
  5 omega  -22.00   14.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  120.0000 24

#__ type_ start__ end____ width___ exp.time_
  6 omega  -65.00  -29.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  120.0000 24

#__ type_ start__ end____ width___ exp.time_
  7 omega   32.00  122.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 60

#__ type_ start__ end____ width___ exp.time_
  8 omega    3.00   30.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -60.0000 18

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   61.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -60.0000 17

#__ type_ start__ end____ width___ exp.time_
 10 omega  -13.00   75.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
 11 omega  -13.00   72.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 12 omega  104.00  129.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 17

#__ type_ start__ end____ width___ exp.time_
 13 omega   44.00  138.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 63

#__ type_ start__ end____ width___ exp.time_
 14 omega   65.00   92.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 18

#__ type_ start__ end____ width___ exp.time_
 15 omega   34.00   88.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega   64.00   89.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 17

#__ type_ start__ end____ width___ exp.time_
 17 omega   43.00   91.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 18 omega   82.00  113.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 21

#__ type_ start__ end____ width___ exp.time_
 19 omega   46.00  103.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
 20 omega  139.00  175.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 24

#__ type_ start__ end____ width___ exp.time_
 21 omega   34.00   94.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
 22 omega  104.00  129.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 17

#__ type_ start__ end____ width___ exp.time_
 23 omega   82.00  110.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -30.0000 19

#__ type_ start__ end____ width___ exp.time_
 24 omega  125.00  150.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 17

#__ type_ start__ end____ width___ exp.time_
 25 omega   76.00  112.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 24

#__ type_ start__ end____ width___ exp.time_
 26 omega  100.00  169.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 27 omega  119.00  144.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  120.0000 17

#__ type_ start__ end____ width___ exp.time_
 28 omega   35.00   92.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 29 omega   63.00  111.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
 30 omega   42.00  118.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000    0.0000 51

#__ type_ start__ end____ width___ exp.time_
 31 omega   35.00   81.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 32 omega   87.00  144.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 33 omega   67.00  106.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   60.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0034729000
_diffrn_orient_matrix_UB_12      -0.0472985000
_diffrn_orient_matrix_UB_13      -0.0769300000
_diffrn_orient_matrix_UB_21      0.0480463000
_diffrn_orient_matrix_UB_22      -0.1021086000
_diffrn_orient_matrix_UB_23      0.0684260000
_diffrn_orient_matrix_UB_31      -0.1486099000
_diffrn_orient_matrix_UB_32      -0.0443636000
_diffrn_orient_matrix_UB_33      0.0513964000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              16
_reflns_limit_k_min              -15
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                6157
_reflns_number_total             6479
_reflns_odcompleteness_completeness 96.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.4115
_refine_diff_density_min         -0.6212
_refine_diff_density_rms         0.0713
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             9.1418
_refine_ls_goodness_of_fit_ref   1.0414
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    71
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.0414
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+1.4454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0890
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C4(H4a,H4b), C7(H7a,H7b), C15(H15a,H15b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C18(H18), C19(H19), C21(H21), C22(H22),
 C24(H24), C25(H25), C26(H26), C29(H29), C30(H30), C33(H33), C34(H34), C35(H35),
  C36(H36)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C23(H23a,H23b,H23c), C37(H37a,H37b,H37c), C38(H38a,H38b,
 H38c)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Pd1 Pd 0.402796(17) 0.152676(14) 0.302410(13) 0.02282(8) Uani 1.000000 .
S1 S 0.20662(7) 0.33284(5) 0.30718(5) 0.03014(15) Uani 1.000000 .
O1 O 0.2636(2) 0.41552(18) 0.32553(18) 0.0439(5) Uani 1.000000 .
O2 O 0.1315(2) 0.24499(17) 0.39385(15) 0.0373(5) Uani 1.000000 .
N1 N 0.3138(2) 0.28905(17) 0.24037(17) 0.0263(5) Uani 1.000000 .
N2 N 0.5384(2) 0.22306(18) 0.35497(17) 0.0276(5) Uani 1.000000 .
N3 N 0.5216(2) 0.02851(17) 0.35731(15) 0.0243(4) Uani 1.000000 .
C1 C 0.2927(3) 0.0714(2) 0.2539(2) 0.0256(5) Uani 1.000000 .
H1 H 0.2928(3) -0.0046(2) 0.2976(2) 0.0307(6) Uiso 1.000000 R
C2 C 0.1446(3) 0.0905(2) 0.2501(2) 0.0279(5) Uani 1.000000 .
H2 H 0.0871(3) 0.1028(2) 0.3080(2) 0.0335(7) Uiso 1.000000 R
C3 C 0.0882(3) -0.0004(2) 0.2319(2) 0.0368(7) Uani 1.000000 .
H3a H 0.1164(3) -0.0687(2) 0.2733(2) 0.0441(8) Uiso 1.000000 R
H3b H -0.0120(3) -0.0040(2) 0.2468(2) 0.0441(8) Uiso 1.000000 R
C4 C 0.1531(3) 0.0294(2) 0.1182(2) 0.0363(7) Uani 1.000000 .
H4a H 0.2039(3) -0.0282(2) 0.1073(2) 0.0436(8) Uiso 1.000000 R
H4b H 0.0833(3) 0.0464(2) 0.0801(2) 0.0436(8) Uiso 1.000000 R
C5 C 0.2492(3) 0.1270(2) 0.0887(2) 0.0281(6) Uani 1.000000 .
H5 H 0.2819(3) 0.1702(2) 0.0153(2) 0.0337(7) Uiso 1.000000 R
C6 C 0.3635(2) 0.0844(2) 0.14405(19) 0.0248(5) Uani 1.000000 .
H6 H 0.3727(2) 0.0113(2) 0.14797(19) 0.0298(6) Uiso 1.000000 R
C7 C 0.1571(3) 0.1812(2) 0.1483(2) 0.0283(6) Uani 1.000000 .
H7a H 0.0691(3) 0.1953(2) 0.1309(2) 0.0340(7) Uiso 1.000000 R
H7b H 0.2018(3) 0.2465(2) 0.1424(2) 0.0340(7) Uiso 1.000000 R
C8 C 0.5083(3) 0.1359(2) 0.10551(18) 0.0250(5) Uani 1.000000 .
C9 C 0.6140(3) 0.0679(2) 0.1042(2) 0.0289(6) Uani 1.000000 .
C10 C 0.7474(3) 0.1046(3) 0.0883(2) 0.0380(7) Uani 1.000000 .
H10 H 0.8171(3) 0.0577(3) 0.0904(2) 0.0456(8) Uiso 1.000000 R
C11 C 0.7798(3) 0.2070(3) 0.0696(3) 0.0424(7) Uani 1.000000 .
H11 H 0.8705(3) 0.2305(3) 0.0608(3) 0.0509(9) Uiso 1.000000 R
C12 C 0.6788(3) 0.2758(2) 0.0635(2) 0.0356(6) Uani 1.000000 .
H12 H 0.7020(3) 0.3475(2) 0.0473(2) 0.0428(8) Uiso 1.000000 R
C13 C 0.5437(3) 0.2423(2) 0.08064(19) 0.0263(5) Uani 1.000000 .
C14 C 0.5915(3) -0.0446(2) 0.1185(2) 0.0342(6) Uani 1.000000 .
H14a H 0.5318(19) -0.0845(5) 0.1850(7) 0.0513(9) Uiso 1.000000 GR
H14b H 0.549(2) -0.0466(3) 0.0675(10) 0.0513(9) Uiso 1.000000 GR
H14c H 0.6787(4) -0.0757(6) 0.1124(17) 0.0513(9) Uiso 1.000000 GR
C15 C 0.4469(3) 0.3291(2) 0.0649(2) 0.0271(5) Uani 1.000000 .
H15a H 0.4908(3) 0.3899(2) 0.0027(2) 0.0325(6) Uiso 1.000000 R
H15b H 0.3648(3) 0.3038(2) 0.0543(2) 0.0325(6) Uiso 1.000000 R
C16 C 0.4017(3) 0.3681(2) 0.1485(2) 0.0292(6) Uani 1.000000 .
H16a H 0.3523(3) 0.4317(2) 0.1247(2) 0.0350(7) Uiso 1.000000 R
H16b H 0.4829(3) 0.3881(2) 0.1640(2) 0.0350(7) Uiso 1.000000 R
C17 C 0.0895(3) 0.3969(2) 0.2364(2) 0.0301(6) Uani 1.000000 .
C18 C 0.1012(3) 0.5056(3) 0.1867(3) 0.0482(8) Uani 1.000000 .
H18 H 0.1719(3) 0.5464(3) 0.1897(3) 0.0579(10) Uiso 1.000000 R
C19 C 0.0084(4) 0.5538(3) 0.1328(3) 0.0512(9) Uani 1.000000 .
H19 H 0.0166(4) 0.6281(3) 0.0987(3) 0.0615(11) Uiso 1.000000 R
C20 C -0.0956(3) 0.4967(3) 0.1273(2) 0.0387(7) Uani 1.000000 .
C21 C -0.1062(3) 0.3884(2) 0.1782(2) 0.0334(6) Uani 1.000000 .
H21 H -0.1779(3) 0.3477(2) 0.1762(2) 0.0401(7) Uiso 1.000000 R
C22 C -0.0139(3) 0.3387(2) 0.2316(2) 0.0294(6) Uani 1.000000 .
H22 H -0.0216(3) 0.2643(2) 0.2651(2) 0.0352(7) Uiso 1.000000 R
C23 C -0.1961(4) 0.5509(3) 0.0683(3) 0.0516(9) Uani 1.000000 .
H23a H -0.1678(16) 0.551(2) 0.0015(8) 0.0774(14) Uiso 1.000000 GR
H23b H -0.2862(7) 0.5138(13) 0.1028(11) 0.0774(14) Uiso 1.000000 GR
H23c H -0.199(2) 0.6236(7) 0.0622(18) 0.0774(14) Uiso 1.000000 GR
C24 C 0.5418(3) 0.3169(2) 0.3576(2) 0.0333(6) Uani 1.000000 .
H24 H 0.4773(3) 0.3637(2) 0.3328(2) 0.0399(7) Uiso 1.000000 R
C25 C 0.6354(3) 0.3503(3) 0.3950(2) 0.0373(7) Uani 1.000000 .
H25 H 0.6346(3) 0.4184(3) 0.3953(2) 0.0448(8) Uiso 1.000000 R
C26 C 0.7286(3) 0.2834(3) 0.4314(2) 0.0355(6) Uani 1.000000 .
H26 H 0.7933(3) 0.3048(3) 0.4570(2) 0.0427(8) Uiso 1.000000 R
C27 C 0.7278(3) 0.1833(2) 0.43064(19) 0.0303(6) Uani 1.000000 .
C28 C 0.6300(3) 0.1557(2) 0.39171(19) 0.0275(5) Uani 1.000000 .
C29 C 0.8195(3) 0.1077(3) 0.4696(2) 0.0358(6) Uani 1.000000 .
H29 H 0.8856(3) 0.1256(3) 0.4961(2) 0.0429(8) Uiso 1.000000 R
C30 C 0.8130(3) 0.0117(3) 0.4690(2) 0.0358(7) Uani 1.000000 .
H30 H 0.8749(3) -0.0371(3) 0.4950(2) 0.0429(8) Uiso 1.000000 R
C31 C 0.7145(3) -0.0183(2) 0.4297(2) 0.0305(6) Uani 1.000000 .
C32 C 0.6223(2) 0.0535(2) 0.39164(18) 0.0260(5) Uani 1.000000 .
C33 C 0.7040(3) -0.1188(2) 0.4295(2) 0.0351(6) Uani 1.000000 .
H33 H 0.7653(3) -0.1692(2) 0.4536(2) 0.0421(8) Uiso 1.000000 R
C34 C 0.6038(3) -0.1425(2) 0.3939(2) 0.0349(6) Uani 1.000000 .
H34 H 0.5958(3) -0.2095(2) 0.3921(2) 0.0418(8) Uiso 1.000000 R
C35 C 0.5135(3) -0.0680(2) 0.3601(2) 0.0288(6) Uani 1.000000 .
H35 H 0.4428(3) -0.0871(2) 0.3380(2) 0.0346(7) Uiso 1.000000 R
O3 O 0.2901(4) -0.2250(3) 0.3434(3) 0.0804(9) Uani 1.000000 .
N4 N 0.3894(3) -0.3096(3) 0.2478(3) 0.0579(8) Uani 1.000000 .
C36 C 0.3725(6) -0.2926(5) 0.3255(4) 0.0828(15) Uani 1.000000 .
H36 H 0.4214(6) -0.3303(5) 0.3730(4) 0.0994(17) Uiso 1.000000 R
C37 C 0.3107(6) -0.2478(4) 0.1728(4) 0.0896(16) Uani 1.000000 .
H37a H 0.3729(9) -0.196(2) 0.1132(14) 0.134(2) Uiso 1.000000 GR
H37b H 0.267(4) -0.2959(6) 0.154(3) 0.134(2) Uiso 1.000000 GR
H37c H 0.241(3) -0.212(3) 0.2028(12) 0.134(2) Uiso 1.000000 GR
C38 C 0.4806(6) -0.3682(4) 0.2085(5) 0.0967(19) Uani 1.000000 .
H38a H 0.4302(6) -0.425(2) 0.205(3) 0.145(3) Uiso 1.000000 GR
H38b H 0.533(3) -0.3226(9) 0.1412(14) 0.145(3) Uiso 1.000000 GR
H38c H 0.542(3) -0.398(3) 0.2515(19) 0.145(3) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 N1 2.055(2) . ?
Pd1 N2 2.177(2) . ?
Pd1 N3 2.095(2) . ?
Pd1 C1 2.053(3) . ?
S1 O1 1.452(2) . ?
S1 O2 1.442(2) . ?
S1 N1 1.581(2) . ?
S1 C17 1.784(3) . ?
N1 C16 1.471(4) . ?
N2 C24 1.325(4) . ?
N2 C28 1.362(3) . ?
N3 C32 1.368(3) . ?
N3 C35 1.333(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.539(3) . ?
C1 C6 1.576(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.551(4) . ?
C2 C7 1.530(4) . ?
C3 H3a 0.9900 . ?
C3 H3b 0.9900 . ?
C3 C4 1.563(4) . ?
C4 H4a 0.9900 . ?
C4 H4b 0.9900 . ?
C4 C5 1.543(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.569(3) . ?
C5 C7 1.533(4) . ?
C6 H6 1.0000 . ?
C6 C8 1.529(3) . ?
C7 H7a 0.9900 . ?
C7 H7b 0.9900 . ?
C8 C9 1.419(4) . ?
C8 C13 1.410(4) . ?
C9 C10 1.397(4) . ?
C9 C14 1.510(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.372(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(4) . ?
C13 C15 1.522(4) . ?
C14 H14a 0.9800 . ?
C14 H14b 0.9800 . ?
C14 H14c 0.9800 . ?
C15 H15a 0.9900 . ?
C15 H15b 0.9900 . ?
C15 C16 1.532(4) . ?
C16 H16a 0.9900 . ?
C16 H16b 0.9900 . ?
C17 C18 1.390(4) . ?
C17 C22 1.380(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(5) . ?
C20 C21 1.386(4) . ?
C20 C23 1.513(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(4) . ?
C22 H22 0.9500 . ?
C23 H23a 0.9800 . ?
C23 H23b 0.9800 . ?
C23 H23c 0.9800 . ?
C24 H24 0.9500 . ?
C24 C25 1.397(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.370(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.400(4) . ?
C27 C28 1.406(4) . ?
C27 C29 1.434(4) . ?
C28 C32 1.429(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.344(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.432(4) . ?
C31 C32 1.406(4) . ?
C31 C33 1.408(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.369(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.395(4) . ?
C35 H35 0.9500 . ?
O3 C36 1.311(7) . ?
N4 C36 1.258(6) . ?
N4 C37 1.518(6) . ?
N4 C38 1.399(6) . ?
C36 H36 0.9500 . ?
C37 H37a 0.9800 . ?
C37 H37b 0.9800 . ?
C37 H37c 0.9800 . ?
C38 H38a 0.9800 . ?
C38 H38b 0.9800 . ?
C38 H38c 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Pd1 N1 94.55(9) . . ?
N3 Pd1 N1 171.12(9) . . ?
N3 Pd1 N2 78.56(8) . . ?
C1 Pd1 N1 92.48(10) . . ?
C1 Pd1 N2 172.44(9) . . ?
C1 Pd1 N3 94.17(9) . . ?
O2 S1 O1 116.50(14) . . ?
N1 S1 O1 113.67(13) . . ?
N1 S1 O2 108.40(12) . . ?
C17 S1 O1 103.67(13) . . ?
C17 S1 O2 106.99(13) . . ?
C17 S1 N1 106.89(12) . . ?
S1 N1 Pd1 121.57(13) . . ?
C16 N1 Pd1 114.17(16) . . ?
C16 N1 S1 116.16(18) . . ?
C24 N2 Pd1 130.09(19) . . ?
C28 N2 Pd1 111.70(18) . . ?
C28 N2 C24 118.2(2) . . ?
C32 N3 Pd1 113.87(18) . . ?
C35 N3 Pd1 128.69(18) . . ?
C35 N3 C32 117.4(2) . . ?
H1 C1 Pd1 106.26(7) . . ?
C2 C1 Pd1 122.83(18) . . ?
C2 C1 H1 106.26(14) . . ?
C6 C1 Pd1 111.66(16) . . ?
C6 C1 H1 106.26(13) . . ?
C6 C1 C2 102.5(2) . . ?
H2 C2 C1 114.67(14) . . ?
C3 C2 C1 107.2(2) . . ?
C3 C2 H2 114.67(15) . . ?
C7 C2 C1 103.7(2) . . ?
C7 C2 H2 114.67(14) . . ?
C7 C2 C3 100.4(2) . . ?
H3a C3 C2 111.11(15) . . ?
H3b C3 C2 111.11(15) . . ?
H3b C3 H3a 109.1 . . ?
C4 C3 C2 103.2(2) . . ?
C4 C3 H3a 111.11(16) . . ?
C4 C3 H3b 111.11(15) . . ?
H4a C4 C3 111.26(16) . . ?
H4b C4 C3 111.26(15) . . ?
H4b C4 H4a 109.2 . . ?
C5 C4 C3 102.5(2) . . ?
C5 C4 H4a 111.26(15) . . ?
C5 C4 H4b 111.26(15) . . ?
H5 C5 C4 115.17(15) . . ?
C6 C5 C4 104.9(2) . . ?
C6 C5 H5 115.17(14) . . ?
C7 C5 C4 98.9(2) . . ?
C7 C5 H5 115.17(15) . . ?
C7 C5 C6 105.7(2) . . ?
C5 C6 C1 102.4(2) . . ?
H6 C6 C1 105.29(13) . . ?
H6 C6 C5 105.29(14) . . ?
C8 C6 C1 113.5(2) . . ?
C8 C6 C5 123.5(2) . . ?
C8 C6 H6 105.29(14) . . ?
C5 C7 C2 95.0(2) . . ?
H7a C7 C2 112.74(13) . . ?
H7a C7 C5 112.74(13) . . ?
H7b C7 C2 112.74(14) . . ?
H7b C7 C5 112.74(14) . . ?
H7b C7 H7a 110.2 . . ?
C9 C8 C6 116.3(2) . . ?
C13 C8 C6 125.2(2) . . ?
C13 C8 C9 118.2(2) . . ?
C10 C9 C8 119.9(3) . . ?
C14 C9 C8 123.5(2) . . ?
C14 C9 C10 116.6(2) . . ?
H10 C10 C9 119.39(17) . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.39(17) . . ?
H11 C11 C10 120.38(17) . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.38(18) . . ?
H12 C12 C11 119.21(18) . . ?
C13 C12 C11 121.6(3) . . ?
C13 C12 H12 119.21(17) . . ?
C12 C13 C8 119.6(2) . . ?
C15 C13 C8 125.5(2) . . ?
C15 C13 C12 114.8(2) . . ?
H14a C14 C9 109.5 . . ?
H14b C14 C9 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C9 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H15a C15 C13 108.03(14) . . ?
H15b C15 C13 108.03(14) . . ?
H15b C15 H15a 107.3 . . ?
C16 C15 C13 117.1(2) . . ?
C16 C15 H15a 108.03(14) . . ?
C16 C15 H15b 108.03(14) . . ?
C15 C16 N1 112.9(2) . . ?
H16a C16 N1 109.00(13) . . ?
H16a C16 C15 109.00(14) . . ?
H16b C16 N1 109.00(14) . . ?
H16b C16 C15 109.00(14) . . ?
H16b C16 H16a 107.8 . . ?
C18 C17 S1 120.1(2) . . ?
C22 C17 S1 120.1(2) . . ?
C22 C17 C18 119.8(3) . . ?
H18 C18 C17 120.43(19) . . ?
C19 C18 C17 119.1(3) . . ?
C19 C18 H18 120.4(2) . . ?
H19 C19 C18 119.1(2) . . ?
C20 C19 C18 121.7(3) . . ?
C20 C19 H19 119.13(18) . . ?
C21 C20 C19 118.2(3) . . ?
C23 C20 C19 120.9(3) . . ?
C23 C20 C21 120.9(3) . . ?
H21 C21 C20 119.50(18) . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.50(17) . . ?
C21 C22 C17 120.1(3) . . ?
H22 C22 C17 119.94(16) . . ?
H22 C22 C21 119.94(18) . . ?
H23a C23 C20 109.5 . . ?
H23b C23 C20 109.5 . . ?
H23b C23 H23a 109.5 . . ?
H23c C23 C20 109.5 . . ?
H23c C23 H23a 109.5 . . ?
H23c C23 H23b 109.5 . . ?
H24 C24 N2 118.40(16) . . ?
C25 C24 N2 123.2(3) . . ?
C25 C24 H24 118.40(18) . . ?
H25 C25 C24 120.52(18) . . ?
C26 C25 C24 119.0(3) . . ?
C26 C25 H25 120.52(18) . . ?
H26 C26 C25 120.22(18) . . ?
C27 C26 C25 119.6(3) . . ?
C27 C26 H26 120.22(16) . . ?
C28 C27 C26 117.9(3) . . ?
C29 C27 C26 123.0(3) . . ?
C29 C27 C28 119.1(3) . . ?
C27 C28 N2 122.2(3) . . ?
C32 C28 N2 117.6(2) . . ?
C32 C28 C27 120.2(2) . . ?
H29 C29 C27 119.56(17) . . ?
C30 C29 C27 120.9(3) . . ?
C30 C29 H29 119.56(17) . . ?
H30 C30 C29 119.42(17) . . ?
C31 C30 C29 121.2(3) . . ?
C31 C30 H30 119.42(17) . . ?
C32 C31 C30 119.5(3) . . ?
C33 C31 C30 122.4(3) . . ?
C33 C31 C32 118.1(3) . . ?
C28 C32 N3 118.1(2) . . ?
C31 C32 N3 122.6(3) . . ?
C31 C32 C28 119.2(2) . . ?
H33 C33 C31 120.62(16) . . ?
C34 C33 C31 118.8(3) . . ?
C34 C33 H33 120.62(17) . . ?
H34 C34 C33 120.11(17) . . ?
C35 C34 C33 119.8(3) . . ?
C35 C34 H34 120.11(18) . . ?
C34 C35 N3 123.3(3) . . ?
H35 C35 N3 118.35(15) . . ?
H35 C35 C34 118.35(18) . . ?
C37 N4 C36 117.6(4) . . ?
C38 N4 C36 132.3(5) . . ?
C38 N4 C37 109.7(4) . . ?
N4 C36 O3 122.6(5) . . ?
H36 C36 O3 118.7(3) . . ?
H36 C36 N4 118.7(3) . . ?
H37a C37 N4 109.5 . . ?
H37b C37 N4 109.5 . . ?
H37b C37 H37a 109.5 . . ?
H37c C37 N4 109.5 . . ?
H37c C37 H37a 109.5 . . ?
H37c C37 H37b 109.5 . . ?
H38a C38 N4 109.5 . . ?
H38b C38 N4 109.5 . . ?
H38b C38 H38a 109.5 . . ?
H38c C38 N4 109.5 . . ?
H38c C38 H38a 109.5 . . ?
H38c C38 H38b 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.279 -0.500 0.500 387.3 83.6 ?


_olex2_date_sample_data_collection 2018-02-01
_olex2_submission_special_instructions 'No special instructions were received'
